Synlett 2011(18): 2652-2656  
DOI: 10.1055/s-0031-1289533
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

An Enantiospecific Approach to Tetraquinane Diterpenes Crinipellins: Synthesis of Norcrinipellins

A. Srikrishna*, V. Gowri
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India
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Publikationsverlauf

Received 4 July 2011
Publikationsdatum:
19. Oktober 2011 (online)

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Abstract

An enantiospecific approach to the synthesis of tetraquinane diterpene crinipellins is described. The cyclopentane ring in campholenaldehyde was identified as the B ring. Two rhodium carbenoid CH insertion reactions for the construction of A and C rings and an intramolecular Michael addition reaction for the D ring of crinipellins were employed as key strategies for the enantiospecific synthesis of norcrinipellins.