Stereodivergent Resolution of Oxabicyclic Ketones: Preparation of Key Intermediates for Platensimycin and Other Natural Products

An improved methodology for the preparation of enantiopure oxabicyclo[3.2.1]octadienes via a stereodivergent resolution is reported. High catalyst control proximal to the oxabridged stereocenter produces readily separable diastereomers in high yield (>92%) and with excellent optical purity (>9...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2013-10, Vol.78 (20), p.10555-10559
Main Authors: VanHeyst, Michael D, Oblak, E. Zachary, Wright, Dennis L
Format: Article
Language:English
Subjects:
Adamantane - chemical synthesis
Adamantane - chemistry
Aminobenzoates - chemical synthesis
Aminobenzoates - chemistry
Anilides - chemical synthesis
Anilides - chemistry
Biological Products - chemistry
Bridged Bicyclo Compounds - chemistry
Ketones - chemistry
Molecular Structure
Stereoisomerism
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:An improved methodology for the preparation of enantiopure oxabicyclo[3.2.1]octadienes via a stereodivergent resolution is reported. High catalyst control proximal to the oxabridged stereocenter produces readily separable diastereomers in high yield (>92%) and with excellent optical purity (>95% ee). This resolution strategy is amenable to large-scale preparations, and the utility of the resolution was further demonstrated in the asymmetric preparation of a key intermediate used in the synthesis of the antibiotic (−)-platensimycin.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4017502