First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine A

Wenyuan Yin; Jun Ma; Felix M Rivas; James M Cook

doi:10.1021/ol062762q

First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine A

Org Lett. 2007 Jan 18;9(2):295-8. doi: 10.1021/ol062762q.

Authors

Wenyuan Yin¹, Jun Ma, Felix M Rivas, James M Cook

Affiliation

¹ Department of Chemistry & Biochemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, USA.

PMID: 17217288
DOI: 10.1021/ol062762q

Abstract

The first enantiospecific total synthesis of the alkaloids 16-epi-vellosimine (1), (+)-polyneuridine (2), (+)-polyneuridine aldehyde (3), and macusine A (4) is reported. The key oxidation was accomplished with the Corey-Kim reagent to provide the important biogenetic intermediates, 16-epi-vellosimine (1) and polyneuridine aldehyde (3), the latter of which is required for the conversion of the sarpagan skeleton into the ajmalan system in the biosynthesis of quebrachidine. [reaction: see text].

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Aldehydes / chemical synthesis*
Aldehydes / chemistry
Alkaloids / chemical synthesis*
Alkaloids / chemistry
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism

Substances

16-epi-vellosimine
Aldehydes
Alkaloids
Indole Alkaloids
polyneuridine
polyneuridine aldehyde
macusine A

Grants and funding

MH 46851/MH/NIMH NIH HHS/United States