Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

2014

Journal or Book Title

Organic Letters

Volume

16

Issue

12

First Page

3248

Last Page

3251

DOI

10.1021/ol501263y

Abstract

Differentially protected 1,2-diols were synthesized by enantioselective aldehyde α-oxygenation followed by organomagnesium or -lithium addition. Contrary to a previous report, the resultant diols possess an anti configuration. Good selectivity was achieved regardless of the hybridization state of the nucleophile or the presence or absence of branching. This method was applied to short syntheses of all possible stereoisomers of two oxylipins from Dracontium loretense with incomplete stereochemical assignments. Spectroscopic comparisons between the synthetic and natural oxylipins led to unambiguous assignments.

Comments

Reprinted (adapted) with permission from Org. Lett., 2014, 16 (12), pp 3248–3251. Copyright 2014 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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