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: skpandey@thapar.edu

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

1H NMR (400 MHz, CDCl3/TMS)

NO2

OH

11

S2

13C NMR (100 MHz, CDCl3)

NO2

O H

11

S3

1H NMR (400 MHz, CDCl3/TMS)

NO2

OTBS

13

S4

13C NMR (100 MHz, CDCl3)

NO2

OTBS

13

S5

1H NMR (400 MHz, CDCl3/TMS)

N

O

14

S6

13C NMR (100 MHz, CDCl3)

N

O

14

S7

1H NMR (400 MHz, CDCl3/TMS)

BocN

OTBS

15

12

N

S8

13C NMR (100 MHz, CDCl3)

BocN

OTBS

15

12

N

S9

1H NMR (400 MHz, CDCl3/TMS)

16

BocN

OH

N

12

S10

13C NMR (100 MHz, CDCl3)

16

BocN

OH

N

12

S11

1H NMR (400 MHz, CDCl3/TMS)

17

BocN

OH

HO

N

12

S12

13C NMR (100 MHz, CDCl3)

17

BocN

OH

HO

N

12

S13

1H NMR (400 MHz, CDCl3/TMS)

HN

O HO

nakinadine B 3 N

12

S14

13C NMR (100 MHz, CDCl3)

HN

O HO

nakinadine B 3 N

12

S15