Regioselective 6-endo cyclizations of 2-indolylacyl radicals: total synthesis of the pyrido[4,3-b]carbazole alkaloid guatambuine

M-Lluïsa Bennasar; Tomàs Roca; Francesc Ferrando

doi:10.1021/jo052428s

Regioselective 6-endo cyclizations of 2-indolylacyl radicals: total synthesis of the pyrido[4,3-b]carbazole alkaloid guatambuine

J Org Chem. 2006 Feb 17;71(4):1746-9. doi: 10.1021/jo052428s.

Authors

M-Lluïsa Bennasar¹, Tomàs Roca, Francesc Ferrando

Affiliation

¹ Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Barcelona 08028, Spain. bennasar@ub.edu

PMID: 16468840
DOI: 10.1021/jo052428s

Abstract

A regioselective 6-endo reductive cyclization of 2-indolylacyl radicals constitutes the key step of a straightforward synthetic entry to the olivacine skeleton, illustrated by a total synthesis of the tetrahydropyridine alkaloid guatambuine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Cyclization
Ellipticines / chemical synthesis
Free Radicals
Indole Alkaloids / chemical synthesis*
Indoles / chemistry

Substances

Alkaloids
Ellipticines
Free Radicals
Indole Alkaloids
Indoles
guatambuine
olivacine