Synthesis of marine polyacetylenes callyberynes A-C by transition-metal-catalyzed cross-coupling reactions to sp centers | Health & Environmental Research Online (HERO)

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Citation
Tags

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

Issue

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.