J Org Chem. 2008 Nov 7;73(21):8661-4. Epub 2008 Oct 8.

Enantioselective synthesis of indolizidine alkaloid trans-209D.

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Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Institute for Research in Biomedicine, and Departament de Química Orgànica, Universitat de Barcelona, Parc Científic de Barcelona c/ Baldiri Reixac, 10, Barcelona 08028, Spain.

Abstract

(S)-N-Boc-baikiain, readily accessible from enantiomerically enriched 2,3-epoxy-5-hexen-1-ol 4 (prepared by Sharpless asymmetric epoxidation), was used as the starting material in the synthesis of indolizidine alkaloid trans-209D , which was obtained in 13 steps and 14% yield from 1 (5% from 4).

PMID:: 18841913; [PubMed - indexed for MEDLINE]

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