Synthesis of (-)-swainsonine and (-)-8-epi-swainsonine from (S)- and (R)-glutamic acid derivatives.
- 1 January 1990
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 38 (10), 2712-2718
- https://doi.org/10.1248/cpb.38.2712
Abstract
(-)-Swainsonine (1) and (-)-8-epi-swainsonine were synthesized from (S)- and (R)-glutamic acid derivatives. (2R,3S,4R)-3,4-Dihydroxy-2-hydroxymethylpyrrolidine derivatives (9a and 9g) were prepared by cis-dihydroxylation of .alpha.,.beta.-unsaturated compounds 6,10 and 15 with OsO4 as the key reaction. The diastereoselective allylation of the aldehydes 18 derived from 9a and 9g, followed by cyclization, gave 1 and (-)-8-epi-swainsonine.This publication has 8 references indexed in Scilit:
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