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Issue 19, 2008
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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

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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 β-hydroxyallenes 12/13 to the corresponding dihydropyrans 14/15.

Graphical abstract: 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

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Publication details

The article was received on 07 May 2008, accepted on 11 Jun 2008 and first published on 11 Jul 2008


Article type: Paper
DOI: 10.1039/B807733A
Citation: Org. Biomol. Chem., 2008,6, 3573-3579

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    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

    Y. Sawama, Y. Sawama and N. Krause, Org. Biomol. Chem., 2008, 6, 3573
    DOI: 10.1039/B807733A

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