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Synlett 2002(2): 0334-0336
DOI: 10.1055/s-2002-19788
LETTER
© Georg Thieme Verlag Stuttgart · New York

Enantio- and Diastereoselective Synthesis of (-)-Semburin and (-)-Isosemburin, Monoterpenes isolated from Swertia japonica

Kohei Kadota, Takahiko Taniguchi, Kunio Ogasawara*
Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Fax: +81(22)2176845; e-Mail: konol@mail.cc.tohoku.ac.jp;
Further Information

Publication History

Received 27 November 2001
Publication Date:
02 February 2007 (online)

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Abstract

An enantio- and diastereocontrolled synthesis of two monoterpenes having a 2,8-dioxabicyclo[3.3.1]nonane framework, (-)-semburin and (-)-isosemburin, isolated from Swertia japonica, has been developed starting from the chiral building block having a 7,8-dioxabicyclo[3.2.1]octane framework.

Key words

chiral building block - intramolecular ene reaction - monoterpene - 7,8-dioxabicyclo[3.2.1]octane framework - 2,8-dioxabicyclo[3.3.1]nonane framework