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Synlett 2000; 2000(7): 1001-1003
DOI: 10.1055/s-2000-6677
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Stereocontrolled Synthesis of a Trihydroxylated Pyrrolizidine Alkaloid, 7-Deoxyalexine

Hidemi Yoda* , Fumihito Asai, Kunihiko Takabe
  • *Department of Molecular Science, Faculty of Engineering, Shizuoka University, Hamamatsu 432-8561, Japan; Fax 8 15 34 78 11 50; E-mail: yoda@mat.eng.shizuoka.ac.jp
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Publication Date:
31 December 2000 (online)

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An enantiomerically and diastereomerically pure route has been developed for the asymmetric synthesis of (1R,2R,3R,7aS)-trihydroxylated pyrrolizidine alkaloid, 7-deoxyalexine, featuring the stereocontrolled elaboration of the functionalized homochiral lactam derived from 2,3,5-tri-O-benzyl-β-d-arabinofuranose.

alexine - pyrrolizidine alkaloid - chiral lactam - nucleophilic addition - arabinofuranose