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Org Lett. 2005 Sep 29;7(20):4423-6.

Enantioselective total synthesis of tricyclic myrmicarin alkaloids.

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1
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA. mavassag@mit.edu

Abstract

[reaction: see text] An enantioselective gram-scale synthesis of a key dihydroindolizine intermediate for the preparation of myrmicarin alkaloids is described. Key transformations in this convergent approach include a stereospecific palladium-catalyzed N-vinylation of a pyrrole with a vinyl triflate, a copper-catalyzed enantioselective conjugate reduction of a beta-pyrrolyl enoate, and a regioselective Friedel-Crafts reaction. The synthesis of optically active and isomerically pure samples of (4aR)-myrmicarins 215A, 215B, and 217 in addition to their respective C4a-epimers is presented.

PMID:
16178549
PMCID:
PMC2992882
DOI:
10.1021/ol051629f
[Indexed for MEDLINE]
Free PMC Article
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