Concise synthesis of the C3-C14-fragment of the antitumor agent laulimalide. Application of Jacobsen's HKR reaction

Authors
Dorling, EK Ohler, E Mantoulidis, A Mulzer, J
Citation
Ek. Dorling et al., Concise synthesis of the C3-C14-fragment of the antitumor agent laulimalide. Application of Jacobsen's HKR reaction, SYNLETT, (7), 2001, pp. 1105-1108
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
7
Year of publication
2001
Pages
1105 - 1108
Database
ISI
SICI code
0936-5214(200107):7<1105:CSOTCO>2.0.ZU;2-D
Abstract
Bromide 3, which represents an appropriately functionalized C3-C14-fragment of the antitumor agent laulimalide (1) has been synthesized from (-)-citro nellal (4) in an overall yield of ca. 17% (12 isolated intermediates). At a very early stage, the synthesis makes use of Jacobsen's HKR reaction to pr oduce epoxide 8 in diastereomerically pure form.