First total synthesis of (R,R,R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product

The first total synthesis of (R,R,R)-bejarol and its (3R,5S,9R)-isomer has been accomplished which confirms the absolute configuration of the natural products. The key step is the gold-catalyzed cycloisomerization of the enantiomerically pure beta-hydroxyallenes 12/13 to the corresponding dihydropyr...

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Veröffentlicht in:Organic & biomolecular chemistry 2008-10, Vol.6 (19), p.3573-3579
Hauptverfasser: Sawama, Yoshinari, Sawama, Yuka, Krause, Norbert
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Sprache:eng
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Zusammenfassung:The first total synthesis of (R,R,R)-bejarol and its (3R,5S,9R)-isomer has been accomplished which confirms the absolute configuration of the natural products. The key step is the gold-catalyzed cycloisomerization of the enantiomerically pure beta-hydroxyallenes 12/13 to the corresponding dihydropyrans 14/15.
ISSN:1477-0520
1477-0539
DOI:10.1039/b807733a