Journal article
Radical-Based Asymmetric Synthesis: An Iterative Approach to 1, 3, 5, ... (2n + 1) Polyols
Organic letters, Vol.1(7), pp.1057-1059
10/07/1999
Handle:
https://hdl.handle.net/2376/106490
PMID: 10825957
Abstract
A conceptually novel approach to 1, 3, 5, ... (2n + 1) polyols based on iterative stereocontrolled homologation of chiral hydroxyalkyl radicals is reported. Starting from α-keto ester precursors, the general sequence of (1) ketone reduction, (2) auxiliary attachment, (3) saponification, (4) Barton esterification, and (5) radical addition provided the two-carbon homologue in 70−80% overall yield. The simplicity and generality of this iterative strategy for 1, 3, 5, ... (2n + 1) polyol synthesis suggests an attractive alternative for the preparation of molecules containing this structural motif.
Metrics
9 Record Views
Details
- Title
- Radical-Based Asymmetric Synthesis: An Iterative Approach to 1, 3, 5, ... (2n + 1) Polyols
- Creators
- Philip GarnerJames T Anderson
- Publication Details
- Organic letters, Vol.1(7), pp.1057-1059
- Academic Unit
- Chemistry, Department of
- Publisher
- American Chemical Society
- Identifiers
- 99900546899201842
- Language
- English
- Resource Type
- Journal article