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Communication | Special issue | Vol 70, No. 1, 2006, pp.153-159
Published online, 21st November, 2006
DOI: 10.3987/COM-06-S(W)49
Total Synthesis of (-)-Dihydrocorynantheol Using Bicyclo[3.2.1]octenone Chiral Building Block

Ayako Tosaka, Shinichiro Ito, Norio Miyazawa, Masatoshi Shibuya, Kunio Ogasawara,* and Yoshiharu Iwabuchi*

*Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

The diastereocontrolled synthesis of (-)-dihydrocorynantheol from a bicyclo[3.2.1]octane chiral building block has been achieved by employing a tandem retro-aldol-Pictet-Spengler reaction-C-3 epimerization sequence as the key step.