Asymmetric synthesis of (+)-galbelgin, (-)-kadangustin J, (-)-cyclogalgravin and (-)-pycnanthulignenes A and B, three structurally distinct lignan classes, using a common chiral precursor

Claire E Rye; David Barker

doi:10.1021/jo200968f

Asymmetric synthesis of (+)-galbelgin, (-)-kadangustin J, (-)-cyclogalgravin and (-)-pycnanthulignenes A and B, three structurally distinct lignan classes, using a common chiral precursor

J Org Chem. 2011 Aug 19;76(16):6636-48. doi: 10.1021/jo200968f. Epub 2011 Jul 22.

Authors

Claire E Rye¹, David Barker

Affiliation

¹ School of Chemical Sciences, University of Auckland, Auckland, New Zealand.

PMID: 21749139
DOI: 10.1021/jo200968f

Abstract

The enantioselective synthesis of three structurally distinct classes of lignan from a single, aza-Claisen-derived, chiral morpholine amide is reported. The class of lignan formed is dependent on the substitution pattern in the aryl rings and choice of protecting group on a key benzylic hydroxyl group. The methodology has been used to asymmetrically synthesize and determine the absolute stereochemistry of lignans (+)-cyclogalgravin 3, (-)-pycnanthulignene A 4, (-)-pycnanthulignene B 5, and (-)-kadangustin J 8.

Publication types

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

MeSH terms

Furans / chemical synthesis*
Furans / chemistry*
Lignans / chemical synthesis*
Lignans / chemistry*
Molecular Structure
Stereoisomerism

Substances

Furans
Lignans
kadangustin J
pycnanthulignene A
pycnanthulignene B
galgravin