enantioselective total synthesis of (s)-nakinadine b

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Electronic Supplementary Information for Enantioselective total Synthesis of (S)-Nakinadine B Yuvraj Garg and Satyendra Kumar Pandey* School of Chemistry and Biochemistry, Thapar University, Patiala 147001, India *Corresponding Author: Telephone number: +91-175-239-3832, Fax No. +91-175-236-4498 E-mail address: [email protected] Table of contents General Experimental 1. 1 H and 13 C spectra for compound 11 S2-S3 2. 1 H and 13 C spectra for compound 13 S4-S5 3. 1 H and 13 C spectra for compound 14 S6-S7 4. 1 H and 13 C spectra for compound 15 S8-S9 5. 1 H and 13 C spectra for compound 16 S10-S11 6. 1 H and 13 C spectra for compound 17 S12-S13 7. 1 H and 13 C spectra for compound 3 S14-S15 S1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2016

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Page 1: Enantioselective total Synthesis of (S)-Nakinadine B

Electronic Supplementary Information for

Enantioselective total Synthesis of (S)-Nakinadine B

Yuvraj Garg and Satyendra Kumar Pandey*

School of Chemistry and Biochemistry, Thapar University, Patiala 147001, India

*Corresponding Author: Telephone number: +91-175-239-3832, Fax No. +91-175-236-4498

E-mail address: [email protected]

Table of contents

General Experimental

1. 1H and 13C spectra for compound 11 S2-S3

2. 1H and 13C spectra for compound 13 S4-S5

3. 1H and 13C spectra for compound 14 S6-S7

4. 1H and 13C spectra for compound 15 S8-S9

5. 1H and 13C spectra for compound 16 S10-S11

6. 1H and 13C spectra for compound 17 S12-S13

7. 1H and 13C spectra for compound 3 S14-S15

S1

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2016

Page 2: Enantioselective total Synthesis of (S)-Nakinadine B

1H NMR (400 MHz, CDCl3/TMS)

NO2

OH

11

S2

Page 3: Enantioselective total Synthesis of (S)-Nakinadine B

13C NMR (100 MHz, CDCl3)

NO2

O H

11

S3

Page 4: Enantioselective total Synthesis of (S)-Nakinadine B

1H NMR (400 MHz, CDCl3/TMS)

NO2

OTBS

13

S4

Page 5: Enantioselective total Synthesis of (S)-Nakinadine B

13C NMR (100 MHz, CDCl3)

NO2

OTBS

13

S5

Page 6: Enantioselective total Synthesis of (S)-Nakinadine B

1H NMR (400 MHz, CDCl3/TMS)

N

O

14

S6

Page 7: Enantioselective total Synthesis of (S)-Nakinadine B

13C NMR (100 MHz, CDCl3)

N

O

14

S7

Page 8: Enantioselective total Synthesis of (S)-Nakinadine B

1H NMR (400 MHz, CDCl3/TMS)

BocN

OTBS

15

12

N

S8

Page 9: Enantioselective total Synthesis of (S)-Nakinadine B

13C NMR (100 MHz, CDCl3)

BocN

OTBS

15

12

N

S9

Page 10: Enantioselective total Synthesis of (S)-Nakinadine B

1H NMR (400 MHz, CDCl3/TMS)

16

BocN

OH

N

12

S10

Page 11: Enantioselective total Synthesis of (S)-Nakinadine B

13C NMR (100 MHz, CDCl3)

16

BocN

OH

N

12

S11

Page 12: Enantioselective total Synthesis of (S)-Nakinadine B

1H NMR (400 MHz, CDCl3/TMS)

17

BocN

OH

HO

N

12

S12

Page 13: Enantioselective total Synthesis of (S)-Nakinadine B

13C NMR (100 MHz, CDCl3)

17

BocN

OH

HO

N

12

S13

Page 14: Enantioselective total Synthesis of (S)-Nakinadine B

1H NMR (400 MHz, CDCl3/TMS)

HN

O HO

nakinadine B 3 N

12

S14

Page 15: Enantioselective total Synthesis of (S)-Nakinadine B

13C NMR (100 MHz, CDCl3)

HN

O HO

nakinadine B 3 N

12

S15