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HERO ID
5732118
Reference Type
Journal Article
Title
Synthesis of marine polyacetylenes callyberynes A-C by transition-metal-catalyzed cross-coupling reactions to sp centers
Author(s)
López, S; Fernandez-Trillo, F; Midón, P; Castedo, L; Saa, C
Year
2006
Is Peer Reviewed?
Yes
Journal
Journal of Organic Chemistry
ISSN:
0022-3263
EISSN:
1520-6904
Volume
71
Issue
7
Page Numbers
2802-2810
Language
English
PMID
16555835
DOI
10.1021/jo052609u
Web of Science Id
WOS:000236652200032
Abstract
Efficient total syntheses of the sponge-derived hydrocarbon polyacetylenes callyberynes A-C have been achieved using metal-catalyzed cross-coupling reactions of highly unsaturated 1,3-diyne fragments as the key steps, namely: Cadiot-Chodkiewicz reaction under Alami's optimized conditions (sp-sp), sequential Sonogashira reaction of a cis,cis-divinyl dihalide (sp2-sp), and Kumada-Corriu reaction of an unactivated alkyl iodide (sp3-sp). This last approach constitutes the first application of a metal-catalyzed sp3-sp Kumada-Corriu cross-coupling reaction to the synthesis of a natural product.
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