Asymmetric Syntheses of (−)-Enterolactone and (7′R)-7′-Hydroxyenterolactone via Organocatalyzed Aldol Reaction

Short syntheses of (−)-enterolactone (1a) and (7′R)-7′-hydroxyenterolactone (1b) have been achieved utilizing organocatalyzed asymmetric cross-aldol reaction of aldehydes 2 and 3 and base-mediated alkylation of lactones 5 and 4.

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2009-10, Vol.74 (20), p.7978-7981
Main Authors: Hajra, Saumen, Giri, Aswini Kumar, Hazra, Sunit
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
4-Butyrolactone - chemistry
Aldehydes - chemistry
Catalysis
Lignans - chemical synthesis
Lignans - chemistry
Molecular Structure
Organic Chemicals
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Short syntheses of (−)-enterolactone (1a) and (7′R)-7′-hydroxyenterolactone (1b) have been achieved utilizing organocatalyzed asymmetric cross-aldol reaction of aldehydes 2 and 3 and base-mediated alkylation of lactones 5 and 4.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900810a