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. 2008 Oct 7;6(19):3573-9.
doi: 10.1039/b807733a. Epub 2008 Jul 11.

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

Yoshinari Sawama  1 , Yuka Sawama, Norbert Krause
Affiliations

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

Yoshinari Sawama et al. Org Biomol Chem. .

Abstract

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.

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