Journal of the American Chemical Society p. 2580 - 2582 (1989)
Update date:2022-07-29
Topics:
Bennett, Richard B.
Choi, Jong-Ryoo
Montgomery, Walter D.
Cha, Jin K.
A practical, enantioselective synthesis of (-)-swainsonine (1) has been achieved in seven steps from 2,3-O-isopropylidene-D-erythorose (6).The key step involves the construction of the bicyclic imine 4 by an intramolecular 1,3 dipolar cycloaddition of azide 5.This study highlights the synthetic utility of the intramolecular 1,3 dipolar cycloaddition of the unactivated olefinic azides in natural product synthesis.
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