Enantioselective Total Synthesis of (+)-Tricycloclavulone

Hisanaka Ito,* Mineki Hasegawa, Yosuke Takenaka, Tatsuya Kobayashi, and Kazuo Iguchi*;
School of Life Science, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
J. Am. Chem. Soc., 2004, 126 (14), pp 4520–4521
DOI: 10.1021/ja049750p
Publication Date (Web): March 18, 2004
Copyright © 2004 American Chemical Society
*

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

, itohisa@ls.toyaku.ac.jp, ; , onocerin@ls.toyaku.ac.jp

Abstract

Abstract Image

The first total synthesis of (+)-tricycloclavulone having a unique tricyclo[5,3,0,01,4]decane skeleton and six chiral centers was achieved in a highly stereoselective manner. It includes a catalytic enantioselective [2+2]-cycloaddition reaction using novel chiral copper catalyst, extremely effecting an intramolecular ester transfer reaction, and asymmetric reduction of the carbonyl group on the α-chain using Noyori's chiral ruthenium catalyst.

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History

  • Published In Issue April 14, 2004
  • Received January 15, 2004

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