An improved total synthesis of (+)-macroline and alstonerine as well as the formal total synthesis of (-)-talcarpine and (-)-anhydromacrosalhine-methine

Xuebin Liao; Hao Zhou; Jianming Yu; James M Cook

doi:10.1021/jo061652u

An improved total synthesis of (+)-macroline and alstonerine as well as the formal total synthesis of (-)-talcarpine and (-)-anhydromacrosalhine-methine

J Org Chem. 2006 Nov 10;71(23):8884-90. doi: 10.1021/jo061652u.

Authors

Xuebin Liao¹, Hao Zhou, Jianming Yu, James M Cook

Affiliation

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

PMID: 17081019
DOI: 10.1021/jo061652u

Abstract

An intramolecular Pd-catalyzed alpha-vinylation process is described. This cyclization has been employed for the enantiospecific total synthesis of gram quantities of both (+)-macroline 3 and the macroline equivalent 4. This sequence is compared to the enolate-driven cross-coupling process. The intermediate 4 was also converted into (-)-alstonerine 1 via modification of an intramolecular Tsuji-Wacker oxidation. This sequence resulted in an improved total synthesis of (-)-talcarpine 5 and (-)-anhydromacrosalhine-methine 6 as well.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Conformation
Stereoisomerism

Substances

Indole Alkaloids
alstonerine
anhydromacrosalhine-methine
talcarpine