appendix 10 10 3.pdf · appendix 10 – spectra related to appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m...

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Appendix 10 – Spectra Related to Appendix 9 APPENDIX 10 Spectra Related to Appendix 9: Studies Toward the Enantioselective Total Synthesis of (+)-Lingzhiol 545

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Page 1: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

APPENDIX 10

Spectra Related to Appendix 9:

Studies Toward the Enantioselective Total Synthesis of (+)-Lingzhiol

545

Page 2: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.1

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 181.

HOTMS 181

546

Page 3: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

020

40

60

80

100

120

140

160

180

200

220

ppm

Figu

re A

10.2

13C

NM

R (5

00 M

Hz,

CD

Cl 3)

of c

ompo

und 181.

547

Page 4: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.3

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 174.

OH

174

548

Page 5: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.4

1 H N

MR

(300

MH

z, C

DC

l 3) o

f com

poun

d 173.

173

O

549

Page 6: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.5

1 H N

MR

(300

MH

z, C

DC

l 3) o

f com

poun

d 172.

172

NOH

550

Page 7: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

020

40

60

80

100

120

140

160

180

200

220

ppm

Figu

re A

10.6

13C

NM

R (5

00 M

Hz,

CD

Cl 3)

of c

ompo

und 172.

551

Page 8: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.7

1 H N

MR

(500

MH

z, C

DC

l 3) o

f com

poun

d 183.

ONM

e

183

552

Page 9: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

020

40

60

80

100

120

140

160

180

200

220

ppm

Figu

re A

10.8

13C

NM

R (5

00 M

Hz,

CD

Cl 3)

of c

ompo

und 183.

553

Page 10: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.8

1 H N

MR

(300

MH

z, C

DC

l 3) o

f com

poun

d 187.

O

O

O OH

187

554

Page 11: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.9

1 H N

MR

(300

MH

z, C

DC

l 3) o

f com

poun

d 188’

.

OOH

188'

555

Page 12: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.1

0 1 H

NM

R (5

00 M

Hz,

CD

Cl 3)

of c

ompo

und 189.

HO

189

OTBS

556

Page 13: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.1

1 1 H

NM

R (5

00 M

Hz,

CD

Cl 3)

of c

ompo

und 190.

HOOTBS

OAc

190

557

Page 14: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.1

2 1 H

NM

R (5

00 M

Hz,

CD

Cl 3)

of c

ompo

und 191.

HOOTBS

OAc

191

558

Page 15: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

020

40

60

80

100

120

140

160

180

200

220

ppm

Figu

re A

10.1

3 13

C N

MR

(125

MH

z, C

DC

l 3) o

f com

poun

d 191.

559

Page 16: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.1

4 1 H

NM

R (5

00 M

Hz,

CD

Cl 3)

of c

ompo

und 192.

HOOTBS

OAc

O192

560

Page 17: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.1

5 1 H

NM

R (5

00 M

Hz,

CD

Cl 3)

of c

ompo

und 193.

HOOTBS

OH

O193

561

Page 18: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

020

40

60

80

100

120

140

160

180

200

220

ppm

Figu

re A

10.1

6 13

C N

MR

(125

MH

z, C

DC

l 3) o

f com

poun

d 193.

562

Page 19: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.1

9 1 H

NM

R (5

00 M

Hz,

CD

Cl 3)

of c

ompo

und 194.

OO

OTBS

OH

194

563

Page 20: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

020

40

60

80

100

120

140

160

180

200

220

ppm

Figu

re A

10.2

0 13

C N

MR

(125

MH

z, C

DC

l 3) o

f com

poun

d 194.

564

Page 21: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.1

7 1 H

NM

R (5

00 M

Hz,

CD

Cl 3)

of c

ompo

und 195.

O

OTBS

OH

O

195

565

Page 22: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

020

40

60

80

100

120

140

160

180

200

220

ppm

Figu

re A

10.1

8 13

C N

MR

(125

MH

z, C

DC

l 3) o

f com

poun

d 195.

566

Page 23: APPENDIX 10 10 3.pdf · Appendix 10 – Spectra Related to Appendix 9 0 1 2 3 4 5 6 7 8 9 1 0 p p m Figure A 10. 1 1 H NMR (500 MHz, CDCl 3) of compound 181. TMS HO 181 546

Appendix 10 – Spectra Related to Appendix 9

01

23

45

67

89

10

ppm

Figu

re A

10.2

1 1 H

NM

R (3

00 M

Hz,

CD

Cl 3)

of c

ompo

und 196.

HOOTBS

N

O

OH

196

567