An unusual reversal of stereoselectivity in a boron mediated aldol reaction: Enantioselective synthesis of the C-1-C-6 segment of the epothilones

Authors
Panicker, B Karle, JM Avery, MA
Citation
B. Panicker et al., An unusual reversal of stereoselectivity in a boron mediated aldol reaction: Enantioselective synthesis of the C-1-C-6 segment of the epothilones, TETRAHEDRON, 56(40), 2000, pp. 7859-7868
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
40
Year of publication
2000
Pages
7859 - 7868
Database
ISI
SICI code
0040-4020(20000929)56:40<7859:AUROSI>2.0.ZU;2-V
Abstract
Enantioselective syntheses of differentially protected C-1-C-6 fragments, ( 3S)-3-hydroxy-4,4-dimethyl-5-oxoheptanoic acid 4, (5S)-7-[1,1-bis(mechyleth yl)-2-methyl-1 -silapropoxy]-5-hydroxy-4,4-dimethylheptan-3-one 5 and (4S)- 2-(2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-3-one 23, common to both ep othilones A and B, are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.