aplicacion de diels alder

8/13/2019 Aplicacion de Diels Alder

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C hapter 2Appl icat ion of Diels AlderCycloaddi t ion Chemistry foreterocyclic Synthesis

L B E R T P D WEm ory University Atlanta GA USA

2 1 I N T R O D U C T I O NThe importance of the Diels-Alder reaction in organic synthesis derives inlarge part f rom its abil ity to generate s ix-m em bered r ings containing several contigu-ous s tereogenic centers in one synthetic operation. In recent years the Diels-A lderreaction of heterosubsti tuted 1 3-dienes and dienophiles has emerge d as a pow erfulm ethod for preparing highly functionalized heterocyclic r ing systems. The aim ofthis chapter is to provide an indication of the wide assortm ent of Diels-Alder chem istrythat has been used for heterocyclic synthesis . Altho ugh som e older references arem entioned the cove rage has been selected from the las t f if teen years including newapplications and modif ication s of older reactions and innovations. The orga nizationof the review is according to s tructural type and represents an extension of an approachused earl ier in Volum e 6 of PHC. Each synthetic sequence is accompanied byreferences to the original li terature. W e hope that you f ind this unusual fo rma t to beuseful.The fo l lowing react ion sequences provide a sampl ing o f some notew or thytransform ations in this area of heterocyclic chem istry.

2 2 R e a c t i o n S c h e m e sI Imino Die/s Aider Rea ct ions I R e v i e w s : B o g e r 87M1 1]W einreb [82TET308 7, 79HE T949]

Im ines as D ienophi les [81TL4607]1) benzeneOMe/ A, 15 h OO P h 3 P = N C OtBu NCO 2tBu ] ~ 2) H3O + , , J ~ N / ~ I

H~ COOEt '~ H jI- ,COO Et + J ' ~ 84 % ;. tBuOOSIMe3 EtO2C OLew is Ac id Cata lyzed Reac t ions of Iminesan ishefsky [82TL3739]

OMe 1.0 eq ZnCI2, THF, ~ ~ 'N'CH2Ph ~ PU. ~. rt, 36-38 h hy IP+ H 69 % OMe3SiO2


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Application o f Diels Alder Cycloaddition Chemistry

Danishefsky - Applicat ion of the aldimine diene cyclocondensation react ion fortotal synthesis [86JOC3915] H

E tO y O S iE t3 ~ . / ' , ~ C 0 2 M eI J , , NZnCI250OMe

OMeHolmes- Syn thesis of piperidine alkaloids using a tosyl imine [87TL813]

0H y C O 2 M e ~ ] 1 O S i M e 3 Le wisacid 1) MeC O3H .

+ " ~ 2) LiAIH4 OHTos~N H3O+ To sN I"CO2Me OH

Grieco - Diels Alder reaction of iminium sa lts generated u nde r Mannich con ditionsin aqueous solut ion [85JACS1768]1.3 eq PhCH2NH2-HCI ~ N

1.3 eq HCHO CH2Ph~ -H2O, 55 ~ 96 h62 %

1.3 eq PhC H2N H2-H CI t ~ N1.3 eq HCHO CH2PhI.rt, 23 h45 %

A chiral am ine as an imino precu rsorO M e ~ , , , , H HCHO/H20

+ H2Nq "Ph 86 % =O N Ph Me_ H

4 9 1

Gr ieco- Cycloconden sation of C acyl iminium ions with cyclopentadiene [86TL1975]O O

+ M e-N H2 HCI H2 0, rt, 22 h Me82 %

4.2 9 1


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Application of D iels Alder Cycloaddition Chem istry 2 3

G r i e c o - Iminium ions derived from aryl amines an d aldehydes function asheterodienes [ 8 8 T L 5 8 5 5 ]

i ~ H 2 0 = ++ M eC NNH2 TFA r t, l h H H H H5equ i v 98 % 3 .7 ' 1

G r i e c o - Intramolecular imino D iels A lder reaction [ 8 5J A C S 1 7 6 8 , 8 6 J O C 3 5 5 3 ]

N H 3C I H C H O / H 20v

50 ~ 48 h H95 % CI

PhCH2NH2, HC I H,,,C H O =EtOH-H2070 ~ N H63 % h

2.5 ' 1

H sa e

N Hh

~ C H O M eNH2 C IH20 /EtOH (1 1)

70 ~66 %

e NDihydrocannivonine

V o l l h a r d t - Oxime ethers a s dienophi les [ 8 0 J A C S 5 2 4 5 ]

S iMe3 ~ N , ,OMeCpCo(CO)2

45 %

MeaSi ~ N'O M e

O HM e 3 S i ~ ~ ~M e3Si ~. . , L~. . , '~ ,~ N, ,OM e


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24 App lication of Diels Alder Cycloaddition Chem istryB o g e r - Vinyl su l fony l imines as aza dienes prepa rat ion f rom the corres pon dingox imes o r unsa tu ra ted a ldehydes [91JACS 1713 ]

OH| M S(O)Ph S02PhM e a n P hS O C I M-20 tO 0 ~ 25 ~

SO2PhH . ~ O PhSO2NH2MgS04 H ~

Ph Ph

Rea ct ion wi th e lect ron r ich d ienophi les$O2Ph SO2Ph

iN ~ ,,.P h E t O , ~ i - P h+ 100 ~CH2 dioxane8 9 %

H OCH2Ph CH2CI2 OCH2Ph12 kbarH M e 2 8% ~ M eL j

M SO2Ph H ,,,~OM e CH2CI2 I12 kbar OM e+ C =II 54 % CH2CH2


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6 Application of Diels Alder Cycloaddition Chemistry

4 2 -C y c l o a d d i t io n e a c t i o n o f v i n y l s o c y a n a t e s w i t h b e n z y n e

5 8 %NCO NH2 Og o o d s y n th o n fo r b e n ~ n e

Magnus - Indole 2 3-quinodim ethane st rategy for synthesis of indole alkaloids[ 84A C R 35 ]1 ' ~ ~ : ~ / ' ~ E N

E+ = HN ~ C H 2 N CH2 NJ RR S i M e RO

N H . . ~ J, 3 , 0 0 ~ ~ , , ~C'3CCH20C OC ' - ''~E t~ I. L I J .. CH2~ ~ / ~ N f 'M e 4 6 %

I IR R

N~ S P h O O

R CH2

I(+)- Aspidosperm idine ]P h S ~

33 ---~/0 E tNIR

I c v l a t i o n l O

,Cl1-C12 bond- . . . . . . . .~, ,,= ~1~,,' ' ~ ? E ' ~ ~ =~ N M e ~ ,,.~ C y cllz atio nl ~ L ~ ~ ' N ~ ' ~ ' ~ ' E tR R

. . . . . . . . . . . . . . . . . . . . . . ~ . . . . . . . . . . . . . . . . . . . . . . . ~ . . . . . . . . . . . . . . . .

KopsanoneandTabersonine

N e ~ E N ~ 'IJ l i-PrNE t, 120 ~ H,,.~ N ' ~ c ,~ o C H ~O C O C , , ~~' ~M CI P h C I ~ ' ~ N J ~ C II IR R


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Application of D iels Alder Cycloaddition Chem istry 7Die/s A ider reactions w ith inverse electron de m andB ra d s h e r Azo nia polycyc l ic arom at ic com pounds a s d ienes [ 5 5 J A C S 4 8 1 2 ,5 8 J A C S 9 3 3 , 6 8 J O C 3 9 0 , 7 3 C C 1 5 6 ]

B r2 R ~ R 1

R ..R1 ( ~ + N ~ ~+ h e a t = B r -R 2 . ~ H 6 6-1 0 0 %

m ixture of stereoisomersHC10 4 r ~ EtQ ~.....H- - + '~20 E t+ C H2=C (O Et)2 .= ~ ' ~ N + . ~ ~

25 ~ 1 h8 9 %C104

Reg ioselective ethoxy groups are nonadjacent o quaternary nitrogen

Cycloaddit ion of isoquinol inium saltsF r a n c k - Use of v iny l su l fides for synthes is of 1 naphthaldehydes [ 8 9 J O C 1 0 9 7 ]

~ t sR ' R tR~ ./~-- H

R 1 = R 2 = H .~ r

1)H+, H202 ) K 2 C O 3 , M e O H , H20

overall 91 %

R 1 CHO

o

Kahn. - Oxidat ive in tram olecular cyc loaddi tion of an azodicarbon yl system[ 8 8 J A C S 1 6 3 8 ]

N H B n C O C O

O Oexo adduct


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8 Application of Diels Alder Cycloaddition ChemistryDie /s A ider reac tion o f n it roso co mpo unds [84JOC4741, 86JAC S1306 , 78TL4767,80JACS3632, 85JACS5534]

t-BuMe2SiO,,N jT OMeCsFr M ecN 0 oC

Note: dihydroxazine ring ad optsa boat like conforma tion to takeadvantage of anomeric effect

~r O Me

83%_ 0 . . O M e _ 0 . . O M e

70 13

Kibayashi- Stereospec if ic to ta l syn thes is o f GT X 223AB [86TL5513]4 -Pr4N 104=

CHCI3H

O

severalsteps

1) Zn, HOAcH 2) BnOCOCI H~ H Na2CO3/CHCI3M sCI , Et3N31H2, Pd/C, MeOHI = ,

Gephyyrotoxin 223AB

W einreb - In t ramolecular N su l f iny l carbamate cyc loaddi t ion [84JOC3243,85TET1173]

S M e ~ l ~ O Hpyridine 0 .,~.x.R / = N ~O - '~ =H~, . ~ o . o c , , ; . - ~ ~ ] ~ 1 7 6 , , . ~ oP C H '~ 1 7 6 O ~ h L ~ c o ~ o o n o n oaminoglycosideantibiotic 66.40 D


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Application of D iels Alder Cycloaddition Chemistry 2 9W ein reb - Use o f N -su l f iny l cyc loadduc ts f o r syn thes i s o f hom oa l l y li c am ines[ 8 3 T L 9 8 7, 8 4 JA C S 7 8 6 1 , 8 4 JO C 3 2 4 3 , 8 5 T E T 1 1 7 3 ]

Me Me O Me. / O -M e M e v ' L ~ 4 / ' 1 ) N a O H M e , ,~ , ,~ l ~ le S ; -S O 2 M e N H T osTosN =S=O = . ~ , M e ~ H . ~ 8 5 % = M eMe PhMe, 0 ~ NT os 2) HaO = _- MeMe . NH Tos ove ra l l MeMe Me H

W ein reb - N-Su l f i ny l compounds as he te rod ienoph i l es [ 8 4 JA C S 7 8 6 1 , 8 4 JO C 3 2 4 3 ,85TET1173 ].o o SOCI2~ . N H2 p y r i d i n e N

15~ '~n .C13(~27- 13H27

r8 5 %n-C13H27

1) PhMgBr2 ) (MeO)3P

8 5 %

n-C13H27~ ~ Oi OH

E.threo .carbam ate

Ba(OH)2Ii

_NH2n-C13H27~OOthreo-Sphingosin

W ein reb - S t e r e o c h e m i c a / c o n t r o / [ 8 4 J A C S 7 8 6 7 ]Me Me

. o - o -S P h M e I [ ~ ~+ II oC- CO2BnNCO2Bn 259 5 %M e M ePhMgBr

H. I~::~ eMe,~Ix. OSPh

H NHCO2Bn2,3-eigmatropic M e + . = 1~ s r /

Me'~NI~ I~O2Bn ]

Note: O nly E-isome r due to reversible[2 3]-sigm atropic rearrangement

P(OMe)3 OHM e O H = M e i ~ ~ ~ M e85 % NHCO2B

threo.hydroxy carbamate


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3 Application o f Diels Alder Cycloaddition Chem istryW e i n r e b - Die ls-Alder adducts o f su l fur d ioxide b is imides) [ 8 4 J A C S 7 8 6 7 ]

M e M e

S ~ 'N R b e n z e n e i I+ ' ocNR 25 RNMe Me

R = T os , C02Me

NHR1 ) P h M g B r . , , ~ . , ~ . M e= M e2) P(OMe)3 NHR

8 3 - 9 2

PhMgBr

M e2 3 -shift

T P(OM e)3

M eH ' ~ i ~ - S p hI - I " "NHR

In term olecu lar [4+2] -Cycloaddi t ions em ploying a-pyrones as d ienesM o o d y 3-Pyr idyne as a d ienophile [ 8 8 J C S ( P 1 ) 2 4 7 ]

N H 2,,v ,,,% N 1) H N O 2 M e 2 N _ N = N ~ NH O 2 C i ~ / , 2 ) M e 2N H72 - H02C ~ ~ ''

H

M 6

M e

BF3-Et20 TA c 2 0 4 4 %O H Me

KOH , & N"H

MeCNA

M 6

M eE i p t i c i n e

- +

M e

M eI s o e l l i p t i c i n e40 % (1 91)


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3 Application o f Diels Alder Cycloaddition Chemistry

T i e t z e - Asym metr ic induction ef fected by remote s tereogenic cen ter [82AC IE22 1]O

O R(R)-Citronellal R = C H l l

DM F w100 ~O R preferential6,6-trans-fused

c y c l oadduc t6 5 %

Ri-de 9 98 %

1) LDA, PhSeCI2) mCPBA-40 ~ to r t

w

46 % R-)- 9R)-Hexahydrocannabinol

T a l l e y o-Quinone m ethide cycloaddition control led by remo te chiral cen ter[ 8 5 J O C 1 6 9 5 ]

HOCF3CO2HM eHCI3 87 %

OH

D a n i s h e f s k y - Lanthanide catalysis [ 8 4 T L 7 2 1 ]

t O ~ l

~ C H O0.05 eq Yb(fod)3,. r t, 80 h E tO ~ /u ~ "

~ 80 %endo product only

= = ~ C H O E I O0.05 eq Yb(fod)3, r t, 80 h

60-80 % mixture endo + exo


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App lication o f Diels Alder Cycloaddition Chemistry 33

I ` ' ` r ~ 1 7 6 IThioketones are ge nerally read ily available to u ndergo the rm al orphotochem ical cycloadditions

R I J R 1 + h v = RR1Vede js - Unstable thioaldehydes can be generated and trapped n situ by aphotochemical method[80JOC2601 8 3 J A C S 6 9 9 9 , 8 2 J A C S 1 4 4 5 , 8 3 J A C S 1 6 8 3 ,8 6 J O C 1 5 5 6 , 8 8 J O C 2 2 2 6 , 8 8 J A C S 5 4 5 2 ]

o ~ ~ h~ o ~~ Y

Vede js - Intramolecu lar hioaldehyde cycloaddition sho ws on ly moderatestereoselectivity [ 8 8 J O C 2 2 2 0 ]hv

p h i ~ +0 12 1)

Vede js - Trapping of thioaldehyde by both Die/s-Aider and ene reactions[ 8 8 J O C 2 2 2 0 ]c.O 2 Et

P h . ~ OO O

H

H

~ S . '401.1)

hv = S i , R = R1O 8 9 O 2 E t

F.. R=RI=H 1R=M e, R =2-methylpropenylM ~ .~ y . .S H in t ra rno lecu lar EtO2C, H retroEtO 2C L ~ ene reaction e . ~ S A Die ls -Alder62 % M =CH2

Ba ldw in - New thermal method for ge nerating thioaldehydes from a lkylthiosu/finates [ 8 2 C C 1 0 2 9 ]


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34 App lication of Diels Alder Cycloaddition Chem istryN e w ta c ti c s f o r e f f e c t i n g Die ls -A lde r reac t ionsD a u b e n - Cycloaddit ions at high pressure [ 8 0 J A C S 7 1 2 6 , 8 5 J O C 2 5 6 7 ]

1) l iq HCN O~ C O 2 M e 2 ) H3PO4 ~ ~ 7 kba r, i1, 24 hS~ _j,,~O = s ~ . ~ o + ~ 03) HC I, AcO H-H20 (10 g scale)4 ) S O C I 2 , A 050

O O Ra-Ni , EtOAc O OO~o , 3 h _.~ ~ ~ O51 overall

(+8 epimer) Canthat~dinKn igh t - Vin yl uran Diels Alder react ions [ 8 8 T L 2 1 0 7 ]

M e O 2 C ' ~ ~290 ~100

M e O 2 C ' ~ ~ ' ~290 ~97

M e O j C / ~ / , ~

Ke a y - High pressure intramolecular Diels A lder react ion of furan as a diene[ 8 9 T L 1 0 4 5 ]O

12 kbarR R2 25 ~

R, R1, R2 = H, Me 43-65

M c C u l lo c h - Diels Alder react ions of pyrroles [ 7 0 C J C 1 4 7 2 ]

CO2Me N CO2MeC AlC la R~~R2 R1 + I II = CO iMeC CH2CI2i i R2 \CO2Me CO iMe 75 CO2MeR 1 = H ; R 2 = M e

R1AICI3 ~ CO2Me85 R2 f. ., , ,~n,~C O 2 Me

H N'cojMe


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App lication of Diels Alder Cycloaddition Chem istry 3 5Kozikowski - Diels-Alder react ion of pyrrole with allene [78JOC2083 ]

0 0r . C O E t i ~ ~ = NN ~ + ~ 70 % CO2Et 75 ~ O2Et

COjEt CO2Et J~ \C O 2E tCO2Et CO2Et CO2Et

Murase - Vinyl pyrro les a s dienes for Die/s-Aider reactions [91CPB489]

S .SC H 2P h = ~/JL'Me /~ CH 2 1) 0 0

BnCI 2) DDQiMe TH F I 2 1 o v e ra l lM e

SCH2Ph

Wuonola - Intram olecu lar [4 2]-cycloaddition of imida zoles [92TL5697]i~ M e 0 M e M e 0M e N ~ N A M e N ~ , ~

220 ~ - HCNN 7O %

Liotta - Tandem Diels-Alderlretro Die/s-Aider reaction of oxazoles [83TL2473]~ O + - - - \Ph OAc 90 %

= PhC =N + O ~ OAc

Ox azole cycloadditions - Synthetic equivalent of 2-aza -1,3-dien esFirestone [67TET943]

M- SO2MeM e S O 2 ~ o 130 ~ U ~ Oe ~ ' ~ O + ~ . -N ~ / 75 % - MeSOiH

O HM e ~ ~ O


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6 Application o f Diels Alder Cycloaddition Chemistry

Jacobi- In tram olecular cyc loaddi t ions w i th oxazoles [84TL4859, 92M I001,81JOC2 065, 78JACS 7748,90JOC202]C: Me 0

6 0 ~M e

H* ==~= 098M e

O

Gnididione

9 4 ~ ' ~ 0 / '~ 0Paniculide-A

OMe 0N OMe

S -) No rsecurinine

I Retro O ie ls-Alder of Oxa zoles IJacobi - Synthes is o f fu rans o r func tiona lit y de rived f rom a s u ~ u r a n[87TET5475 ] ~ O ~ o

~ PhEt _ Me,,, ,~~N)J~OMe ref lux

1) NaBH4 ,.- M e C N 2 ) p H 59 4 H

O H . . ~O O

HPaniculide A


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Application o f Diels Alder Cycloaddition Chemistry 7

Diels-Alder of Thiazole DerivativesJacobi - Form at ion of fused r ing thiophenes [84HET281, 88TET3327, 87TL2937]

M e ~ O E t O E tN~ ,S

R - M e C NR = CH2OMeI O 5 7 %

M e ~ ~ O ~ Me 74

H Hi ~ Ra-Ni_

8 5 % - MeMe ~en~U~ Me

1 ' 1

Intramolecular Ko ndrat eva Pyr idine Syn thesis [57MI666, 59MI484]W einreb - Add ition of DB N is helpful to intramolecular cycloadd itions [ 89JO05580 ]

~~ 1'~ N,, Ac

OTBS

Ao-DCBDBN

.,Ac

OTBS

A-H20

~ N A c

OTBSNOTE: oxazo les bea ring an EWG at C4 are unreactive n cycloadditions.

I e t e r ~ c t i ~ ICycload dit ions involving h eteroarom atic azad ienes. Rev iew: Boge r [86CR781]Sauer [69TL5171]

49--*7./o 'pyrrolidineCO2Me CO2Me


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38 Application of D iels Alder Cycloaddition ChemistryBoger - Die/s-Aider react ions of heterocyclic azadienes for the total synthesis ofcomplex molecules [87JACS2717] NH

1) H2S, E t 2 N H ~ ~ ~ ' S M eNO2 dioxane _- NO2 N +2) M el, MeCNMeO ~ '~ 4 2 % M e O ~

CO2MeN ~ - NN . , ~ NMeO2C

dioxane80 ~ 22 h82 %

R 2 N , ~ M e4 eq ~OBn

~ O M eO M e

CH2CI , 6.2 Kbarrt, 120 hID65 %

( 2 . 8 1 )

IN.< CO2Me

[~OBn~ O M eO M e

10 stepsI=

0M e O ~

0 NH ~Me

Streptonigrin OMe

Indole as a dien oph ile n inverse electron demand D ie/s-Aider react ionSnyder [90JOC3257]

CO2Me CO2Me

R CO tMe CO2MeR = B z

Inverse electron dem and 4 2 react ions of pyridazinesNeunhoef fe r [73LAC1955]

R1R21~ / N I~1 + M e2N ~ H2110Me

57-93 %X = NMe2,OMe

9 1R 2 ~ x

NO TE: Dim ethyl aniline derivative forme d predominantly.


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App lication o f Diels Alder Cycloaddition Chemistry 39Neunhoeffer - React ion of d im ethy l pyr idaz ine 4,5-d icarboxy lic ac id d imethy les te r w i th an yn am ine [72TL1517, 73LAC437]

N~ ~C O 2 Me MeC_=CNEt2N~,,,, '~CO2Me

. C 0 2 M eM e O 2 C N . ~ N Et2 -N2

e

M e O 2 C , , ~ ~ N E t 2MeO2C ~ Me

Inverse electron de m an d 4 2 reactions o f 1,2,4,5-tetrazines [84MI550 ,78MI1095 ]Sauer [66TL4979]

R ,,sN RN R ~ R 1N ~ N R 1C H =C H R N . I ~ ..R1 N2N ~ N = 1 ~ T L ' .. ~ N. .R RDie/s-Aider reactions of e lectron def ic ient heteroarom at ic d ienesRof fey [69JHC 497] , Se i tz [79AP452] , Sauer [84TL2541, 83TL1481, 75TL2897]

EtO ll/Ph r ,N CO2Me/ I~1/CO 2M e N~I ', ,NNH N2LMeO2C Ph 27 % CO2MeCO2Me

N J ~NN ~ I NCO2Me r 1' y ~ ,b C O ~ M ,,=- N . = - ~ N . . N M e 2 /

R = alkyl, Ph jN2 =

5 6 - 8 1 %

C O 2 M eN ~ N ..N M e2CO2Me

Ta ylor - Rou te to con dens ed pyraz ines v ia in ternal cyc loaddi tions us ing n i t ri les asdienophi les [ 89J OC12 45 , 86J OC1967 ]CN

Ph,,,,,~N,,N L x 2 2 5 . 2 3 5 o c P h,. N , . ~ X

X = O , NCOCF


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40 Application o f Diels-A lder Cycloaddition Chem istry

2 3 R e f e r e n c e s55JACS481257MI66658JACS93359MI48466TL497967TET94368JOC39069JHC49769TL517170CJC147272TL151773CC15673LAC43773LAC195575TL289778JACS774878JOC208378MI109578TL476779AP45279JACS507379HET94980JACS363280JACS524580JACS712680JOC260181JACS638781JOC206582ACIE22182CC102982JACS 144582JACS706582TET308782TL3739

C. K. Bradsh aw, L. E. B eavers, J. Am. Chem . Soc. 1955, 77,4812.G. Y. Kond rat eva Khim. Prom. (Moscow) 1957, 2, 666.C. K. Bradsher, T. W. G . Solom ons, J. Am. Che m. Soc.1958, 80 933.G. Y. Kond rat eva Izv. Akad. Nauk. SSSR Ser . Khim. 1959,484.J. Sauer, G. Heinrichs, Tetrahedron Lett. 1966, 4979.R. A. Firestone, E. E. Harris, W. Reuter, Tetrahedron 1967,23 943.D. L. Fields, T. H. Regan, J. C. Dignan, J. Org. Chem. 1968,33 390.P. Roffey , J. P. Verg e, J. Heterocycl. Chem. 1969, 6, 497.W. D ittmar, J. Sauer, A. Steigel Tetrahedron Lett. 1969,5171.R. C. Bansal, A. W. McCulloch, A. G. McInnes, Ca n. J.Chem. 1970, 48 1472.H. Neunhoeffer, G. Werner, Tetrahedron Lett. 1972, 1517.C. K. Bradsher, F. H. Day , A. T. McP hail, P. S. W ong , J.Chem. Soc. Chem. Comm un. 1973, 156.H. Neunhoeffer, G. Werner, Liebigs Ann. Che m. 1973, 437.H. Neunhoeffer, G. Werner, Liebigs Ann. Che m. 1973, 1955.. Burg, W . Dittmar, H. R eim, A. S teigel, J. Sauer, Tetrahe-dron Lett . 1975, 2897.P. A. Jacobi, T. Craig, J. Am. Chem. Soc. 1978, I00 7748.A. P. Koz ikowsk i, M. P. Kuniak, J. Org. Chem. 1978, 432083.H. Neunhoeffer, Chemistry of Heterocyclic Compounds;W iley: Ne w York, 19 78; Vol. 33 pp 1095-1097.G. E. Keck, Tetrahedron Lett. 1978, 4767.G. Seitz, W. Overhe u, Arch. Pharm. 1979, 312 452.S. M. W einreb, N. A. Khatri, H . Shringa rpure, J. Am. Chem.Soc. 1979, 101 5073.S. M. Weinreb, J. I. Levin, Heterocycles 1979, 12, 949.G. E. Keck, D. G. Nickell, J. Am. Chem . Soc. 1980, 1023632.K. P. C. Vollhardt, R. L. Funk, J. Am. Chem. Soc. 1980, 1025245.W. G. Da uben, C. R. Kessel, K. H. Tak em ura, J. Am. Chem.Soc. 1980 102 7126.E. Vedejs, M. J. Am ost, M . Dolphin, J. Eustache, J. Org.Chem. 1980, 45 2601.N. A. Khatri, H. F. Schm itthener, J. Schringarp ure, S. M.W einreb, J. Am. Chem . Soc. 1981, 103 6387.P. A. Jacobi, D. G. Walker, I. M. A. Odeh, J. Org. Chem.1981, 46 2065.L. F. Tietze, G. von K iedrowsk i, B. Berger, Angew. Chem.Int. Ed. 1982 21 221.J. E. Baldwin, R. C. G. Lopez, J. Chem . Soc. Chem.Commun. 1982, 1029.E. Vedejs, T. H. Eberlein, D. L. Vanle, J. Am. Chem. Soc.1982, 104 1445.R. A. Gobao, M. L. Bremmer, S. M. Weinreb, J. Am. Chem.Soc. 1982, 104 7065.S. M. Weinreb, R. R. Staib, Tetrahedron 1982, 38 3087.J. F. Kerwin, S. J. Dan ishefsky Tetrahedron Lett. 1982, 23


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App l icat ion o f Diels -Alder Cycloaddi t ion Chemis try 41

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