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S1
A Stereocontrolled Access to Functionalized Macrolactams via Aza-
Claisen Rearrangement
Young-Ger Suh,*a Yong-Sil Lee,a Seok-Ho Kim,b Jae-Kyung Jung,c
Hwayoung Yun,a Jaebong Jang,a Nam-Jung Kima and Jong-Wha Jung*a
aCollege of Pharmacy, Seoul National University, Gwanakro 599, Gwanak-Gu, Seoul
151-742, Korea, bDepartment of Pharmacy, College of Pharmacy, CHA University,
Haeryongro 120, Pocheon-si, Gyeongi-do, 487-010, Korea, cCollege of Pharmacy,
Chungbuk National University, Cheongju 361-763, Korea
E-mail: ygsuh@snu.ac.kr
Supporting Information
1H- and 13C-NMR Spectra
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S2
1H-NMR and 13C-NMR Spectra
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
NBoc
7
8a
NBoc
7
8a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S3
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
NBoc
8
8b
NBoc
8
8b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S4
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
N9Boc
8c
N9Boc
8c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S5
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
N7
O
Me
9a
N7
O
Me
9a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S6
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
N8
O
Me
9b
N8
O
Me
9b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S7
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
N9
O
Me
9c
N9
O
Me
9c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S8
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
N
CHO7
O
Me
10a
N
CHO7
O
Me
10a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S9
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
N
CHO8
O
Me
10b
N
CHO8
O
Me
10b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S10
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
CHO
N9
O
Me
10c
CHO
N9
O
Me
10c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S11
▲ 1H-NMR (300 MHz, CDCl3)
▲ 1H-NMR (300 MHz, CDCl3)
N7
O
Me
OTBS
11a
N8
O
Me
OTBS
11b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S12
▲ 1H-NMR (300 MHz, CDCl3)
▲ 1H-NMR (300 MHz, CDCl3)
N9
O
Me
OTBS
11c
N7
O
Me
OTBS
12a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S13
▲ 1H-NMR (300 MHz, CDCl3)
▲ 1H-NMR (300 MHz, CDCl3)
N9
O
Me
OTBS
12c
NH
O
Me7 4
OTBS
13a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S14
▲ 13C-NMR (75 MHz, CDCl3)
▲ 1H-NMR (300 MHz, CDCl3)
N8
O
MeH
OTBS
4
13b
NH
O
Me7 4
OTBS
13a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S15
▲ 13C-NMR (100 MHz, CDCl3)
▲ 1H-NMR (300 MHz, CDCl3)
N9
O
MeH
OTBS
4
13c
N8
O
MeH
OTBS
4
13b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S16
▲ 13C-NMR (100MHz, CDCl3)
▲ 1H-NMR (300MHz, CDCl3)
NH
O
Me7 4
OTBS
14a
N9
O
MeH
OTBS
4
13c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S17
▲ 13C-NMR (75 MHz, CDCl3)
▲ 1H-NMR (400 MHz, CDCl3)
N
OTBS
Me
OH
8 4
14b
NH
O
Me7 4
OTBS
14a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S18
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
N9
O
MeH
OTBS
4
14c
N9
O
MeH
OTBS
4
14c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S19
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (100 MHz, CDCl3)
NBoc
O
Me
Me
23
NBoc
O
Me
Me
23
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S20
▲ 1H-NMR (300 MHz, CDCl3)
▲ 13C-NMR (75 MHz, CDCl3)
NH
Me
Me
26
NH
Me
Me
26
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S21
▲ 1H-NMR (400 MHz, CDCl3)
▲ 1H-NMR (400 MHz, CDCl3)
N
Me
Me
OTBS
Me
O17
N
Me
Me
OTBS
Me
OH
18
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S22
▲ 13C-NMR (125 MHz, CDCl3)
▲ 1H-NMR (400 MHz, CDCl3)
23
NH
O
Me
Me
OTBS
Me
N
Me
Me
OTBS
Me
OH
18
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S23
▲ 13C-NMR (100 MHz, CDCl3)
▲ 1H-NMR (300 MHz, CDCl3)
23
NH
O
Me
Me
OTBS
Me
N
Me
Me
Me
O
OTBS
20
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S24
▲ 1H-NMR (500 MHz, CDCl3)
▲ 13C-NMR (75 MHz, CDCl3)
N
Me
Me
OTBS
Me
OH
21
N
Me
Me
OTBS
Me
OH
21
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S25
▲ 1H-NMR (500 MHz, CDCl3)
▲ 13C-NMR (75 MHz, CDCl3)
N
Me
Me
OTBS
Me
OH
24
N
Me
Me
OTBS
Me
OH
24
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S26
▲ 1H-NMR (400 MHz, CDCl3 + CD3OD)
NH
O
Me
Me
OH
Me
Fluvirucinine A1 (19)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S27
▲ 13C-NMR (75 MHz, CDCl3 + CD3OD)
NH
O
Me
Me
OH
Me
Fluvirucinine A1 (19)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S28
▲ 1H-NMR (400 MHz, CDCl3)
3-epi-Fluvirucinine A1 (22)
O
NHMe
Me
Me
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
S29
▲ 13C-NMR (75 MHz, CDCl3)
3-epi-Fluvirucinine A1 (22)
O
NHMe
Me
Me
OH
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011
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