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Letter

Stereoselective Total Synthesis of (−)-Perrottetinene and Assignment of Its Absolute Configuration

Supporting Info

Yanling Song,^†^‡ Soonho Hwang,^† Ping Gong,^‡ Deukjoon Kim,^† and Sanghee Kim*^†

College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea, and School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Liaoning 110016, P. R. China

Org. Lett., 2008, 10 (2), pp 269–271

DOI: 10.1021/ol702692q

Publication Date (Web): December 18, 2007

Copyright © 2008 American Chemical Society

†

Seoul National University.

,

‡

Shenyang Pharmaceutical University.

,

*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, pennkim@snu.ac.kr

Abstract

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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 γ-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.

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History

Published In Issue January 17, 2008
Received November 6, 2007

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