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ChemInform Abstract: Stereocontrolled Synthesis of a Trihydroxylated Indolizidine Alkaloid, 1-Deoxycastanospermine.

✍ Scribed by H. YODA; T. NAKAJIMA; K. TAKABE

Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Stereocontrolled Synthesis of a Trihydroxylated Indolizidine Alkaloid, 1-Deoxycastanospermine.

-A novel procedure for the synthesis of 1-deoxycastanospermine (IX), which is of interest in the treatment of AIDS, is described starting from the D-tartaric acid derivative (I). The key feature of the process is the nucleophilic addition of vinylmagnesium bromide to the N-Boc lactam (II) providing a labile quaternary Ξ±-hydroxypyrrolidine and its completely stereoselective NaBH4/CeCl3 reduction to the desired (3S)stereoisomer (IV). -(YODA, H.;

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