Improved synthesis of the northern hemisphere of epothilone A by a sharpless asymmetric dihydroxylation

Authors
Quitschalle, M Kalesse, M
Citation
M. Quitschalle et M. Kalesse, Improved synthesis of the northern hemisphere of epothilone A by a sharpless asymmetric dihydroxylation, TETRAHEDR L, 40(44), 1999, pp. 7765-7768
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
44
Year of publication
1999
Pages
7765 - 7768
Database
ISI
SICI code
0040-4039(19991029)40:44<7765:ISOTNH>2.0.ZU;2-D
Abstract
An improved synthesis of the northern hemisphere of epothilone A is describ ed. This approach utilizes the Sharpless asymmetric dihydroxylation of 5-he xen-2-one (allyl acetone) to generate the precursor for the Wittig reaction and the subsequent ring closing metathesis reaction (RCM). This strategy a llows to generate precursor 13 as both enantiomers from ready available sta rting material in a very efficient manner. (C) 1999 Elsevier Science Ltd. A ll rights reserved.