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Synlett 1997; 1997(8): 911-912
DOI: 10.1055/s-1997-962
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Stereocontrolled Synthesis of a Trihydroxylated Indolizidine Alkaloid, 1-Deoxycastanospermine

Hidemi Yoda* , Tomohito Nakajima, Kunihiko Takabe
  • *Department of Molecular Science, Faculty of Engineering, Shizuoka University, Hamamatsu 432, Japan, Fax: 81 53 478 1189; E-mail: tchyoda@eng.shizuoka.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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An efficient and novel process is described for the asymmetric synthesis of (6S,7R,8R,8aR)-6,7,8-trihydroxyindolizidine alkaloid, 1-deoxycastanospermine in 22% overall yield based on the C2-imide featuring the completely stereoselective reduction of an α-hydroxypyrrolidine intermediate elaborated through asymmetric deoxygenation of a quaternary α-hydroxylactam.

indolizidine alkaloid - 1-deoxycastanospermine - deoxygenation - α-hydroxypyrrolidine - C2-imide