Transannular Diels−Alder Studies on the Asymmetric Total Synthesis of Chatancin:  The Pyranophane Approach

Transannular Diels−Alder Studies on the Asymmetric Total Synthesis of Chatancin:  The Pyranophane Approach

A pathway is proposed for the biosynthesis of (+)-chatancin and (+)-sarcophytin linking these tetracycles to cembranoids by a pyranophane transannular Diels−Alder reaction. Preliminary synthetic results in this direction to reach macrocyclic dienedione 28 from farnesol are reported. Major synthetic...

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Veröffentlicht in:Organic letters 2000-09, Vol.2 (18), p.2737-2740
Hauptverfasser: Toró, András, L'Heureu, Alexandre, Deslongchamps, Pierre
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Cnidaria - chemistry
Crystallography, X-Ray
Diterpenes - chemical synthesis
Diterpenes - chemistry
Farnesol - chemistry
Platelet Activating Factor - antagonists & inhibitors
Stereoisomerism
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Zusammenfassung:A pathway is proposed for the biosynthesis of (+)-chatancin and (+)-sarcophytin linking these tetracycles to cembranoids by a pyranophane transannular Diels−Alder reaction. Preliminary synthetic results in this direction to reach macrocyclic dienedione 28 from farnesol are reported. Major synthetic steps include a Prins reaction, two enantioselective hydrogenations, and a macrocyclization via a β-ketosulfoxide Michael-addition on an enone.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol006220z