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Issue 10, 2007
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Golden opportunities in natural product synthesis: first total synthesis of (–)-isocyclocapitelline and (–)-isochrysotricine by gold-catalyzed allene cycloisomerization

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Abstract

The first enantioselective total syntheses of the β-carboline alkaloids (–)-isochrysotricine (1) and (–)-isocyclocapitelline (2) are reported which confirm the absolute configuration of these natural products. Key steps are the copper-mediated SN2′-substitution of propargyl oxiranes13/14 and the gold-catalyzed cycloisomerization of α-hydroxyallene 15, resulting in a highly efficient center-to-axis-to-center chirality transfer.

Graphical abstract: Golden opportunities in natural product synthesis: first total synthesis of (–)-isocyclocapitelline and (–)-isochrysotricine by gold-catalyzed allene cycloisomerization

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Publication details

The article was received on 16 Mar 2007, accepted on 03 Apr 2007 and first published on 16 Apr 2007


Article type: Communication
DOI: 10.1039/B703995F
Org. Biomol. Chem., 2007,5, 1519-1521

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    Golden opportunities in natural product synthesis: first total synthesis of (–)-isocyclocapitelline and (–)-isochrysotricine by gold-catalyzed allene cycloisomerization

    F. Volz and N. Krause, Org. Biomol. Chem., 2007, 5, 1519
    DOI: 10.1039/B703995F

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