An aldol approach to the synthesis of the EF fragment of spongistatin 1

Citation
Mt. Crimmins et al., An aldol approach to the synthesis of the EF fragment of spongistatin 1, ORG LETT, 3(6), 2001, pp. 949-952
Citations number
55
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
6
Year of publication
2001
Pages
949 - 952
Database
ISI
SICI code
1523-7060(20010322)3:6<949:AAATTS>2.0.ZU;2-Q
Abstract
[GRAPHICS] A synthesis of the C29-C51 fragment of spongistatin 1, containing the E and F rings, has been completed. The approach relies on four diastereoselectiv e aldol additions and an asymmetric glycolate alkylation to establish eight of the eleven stereogenic centers. The intact chlorodiene side chain was a ppended by a Lewis acid catalyzed addition of an allylstannane to an epoxy enol ether.