Approach towards the total synthesis of rhizoxin: Enantioselective preparation of the lactone core

Authors
Zoutani, MAN Pancrazi, A Ardisson, J
Citation
Man. Zoutani et al., Approach towards the total synthesis of rhizoxin: Enantioselective preparation of the lactone core, SYNLETT, (6), 2001, pp. 769-772
Citations number
50
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
6
Year of publication
2001
Pages
769 - 772
Database
ISI
SICI code
0936-5214(200106):6<769:ATTTSO>2.0.ZU;2-O
Abstract
The construction of the C1-C10 lactone core of rhizoxin, a 16-membered anti tumoral macrolide, is reported. The strategy is based on the installation o f the C7 and C8 asymmetric centers with a Brown allylation reaction. The C5 asymmetric carbon was controlled during a lactonisation step, leading to t he equatorial chain at C5. Homologation sequences at C3 and C9 were perform ed via a Wadsworth-Emmons and a Takai reaction, respectively.