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Paper | Special issue | Vol 56, No. 1-2, 2002, pp.209-220
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)18
High-Pressure Mediated Asymmetric Diels-Alder Reaction of Chiral Sulfinylacrylate Derivatives and Its Application to Chiral Synthesis of (-)-COTC and (-)-Gabosine C

Tamiko Takahashi,* Yoko Yamakoshi, Kazuya Okayama, Junko Yamada, Wei-Ying Ge, and Toru Koizumi

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0194, Japan


The asymmetric Diels-Alder reactions of chiral sulfinylacrylate derivatives (1 and 2) with dienes (3-12) were examined under high-pressure (1.2 GPa) conditions. The endo cycloadduct (13e) obtained from sulfinyl acrylate (1) and 2-methoxyfuran (5) was converted to (-)-COTC (25) and (-)-gabosine C (26).