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Org Lett. 2008 Jan 17;10(2):269-71. Epub 2007 Dec 18.

Stereoselective total synthesis of (-)-perrottetinene and assignment of its absolute configuration.

Author information

1
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea.

Abstract

The first stereoselective total synthesis of the bibenzyl tetrahydrocannabinol, (-)-perrottetinene, has been achieved from readily available starting materials. The absolute stereochemistry is derived from a chiral gamma-hydroxy vinylstannane. The key reaction is the synthesis of the cis-disubstituted cyclohexene ring of perrottetinene by diastereoselective Ireland-Claisen rearrangement and a ring-closing metathesis reaction. The absolute configuration of (-)-perrottetinene is proposed.

PMID:
18085788
DOI:
10.1021/ol702692q
[Indexed for MEDLINE]

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