Stereocontrolled synthesis of an indole moiety of sespendole and stereochemical assignment of the side chain

Masaatsu Adachi; Keiko Higuchi; Nopporn Thasana; Hitomi Yamada; Toshio Nishikawa

doi:10.1021/ol202895u

Stereocontrolled synthesis of an indole moiety of sespendole and stereochemical assignment of the side chain

Org Lett. 2012 Jan 6;14(1):114-7. doi: 10.1021/ol202895u. Epub 2011 Nov 29.

Authors

Masaatsu Adachi¹, Keiko Higuchi, Nopporn Thasana, Hitomi Yamada, Toshio Nishikawa

Affiliation

¹ Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.

PMID: 22126279
DOI: 10.1021/ol202895u

Abstract

Two possible diastereomers of the indole moiety of sespendole were synthesized from 3-hydroxy-4-nitrobenzaldehyde in a highly stereoselective manner. Comparison of (1)H and (13)C NMR spectra of the two synthetic materials with those sespendole leads us to propose that the relative stereochemistry of the epoxyalcohol is syn.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Diterpenes / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Stereoisomerism

Substances

Diterpenes
Indoles
sespendole