Synthesis of Marine Polyacetylenes Callyberynes A−C by Transition-Metal-Catalyzed Cross-Coupling Reactions to sp Centers

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−s...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2006-03, Vol.71 (7), p.2802-2810
Main Authors: López, Susana, Fernández-Trillo, Francisco, Midón, Pilar, Castedo, Luis, Saá, Carlos
Format: Article
Language:English
Subjects:
Animals
Catalysis
Chemistry
Exact sciences and technology
Molecular Structure
Organic chemistry
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Polyacetylenes - chemical synthesis
Polyacetylenes - chemistry
Porifera - chemistry
Stereoisomerism
Transition Elements - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo052609u