First Stereoselective Syntheses of (−)-Siphonodiol and (−)-Tetrahydrosiphonodiol, Bioactive Polyacetylenes from Marine Sponges

First Stereoselective Syntheses of (−)-Siphonodiol and (−)-Tetrahydrosiphonodiol, Bioactive Polyacetylenes from Marine Sponges

The first stereoselective total syntheses of the bioactive marine polyacetylenes (−)-siphonodiol and (−)-tetrahydrosiphonodiol were achieved using highly convergent approaches based on optimized Cadiot−Chodkiewicz and sequential Sonogashira cross-coupling reactions.

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Veröffentlicht in:Journal of organic chemistry 2005-08, Vol.70 (16), p.6346-6352
Hauptverfasser: López, Susana, Fernández-Trillo, Francisco, Midón, Pilar, Castedo, Luis, Saá, Carlos
Format: Artikel
Sprache:eng
Schlagworte:
Acetylene - analogs & derivatives
Acetylene - chemical synthesis
Acetylene - chemistry
Acetylene - pharmacology
Aliphatic compounds
Animals
Chemistry
Exact sciences and technology
Marine Biology
Molecular Structure
Organic chemistry
Polyacetylenes
Polymers - chemical synthesis
Polymers - chemistry
Polymers - pharmacology
Porifera - chemistry
Preparations and properties
Seawater
Stereoisomerism
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Beschreibung
Zusammenfassung:The first stereoselective total syntheses of the bioactive marine polyacetylenes (−)-siphonodiol and (−)-tetrahydrosiphonodiol were achieved using highly convergent approaches based on optimized Cadiot−Chodkiewicz and sequential Sonogashira cross-coupling reactions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050807f