Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families

Phil S Baran; Jeremy M Richter

doi:10.1021/ja047874w

Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families

J Am Chem Soc. 2004 Jun 23;126(24):7450-1. doi: 10.1021/ja047874w.

Authors

Phil S Baran¹, Jeremy M Richter

Affiliation

¹ Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. pbaran@scripps.edu

PMID: 15198586
DOI: 10.1021/ja047874w

Abstract

The invention of a method for the direct union of indoles and carbonyl compounds (ketones, amides, esters) is described. Using this new method, a short, enantioselective, gram-scale and protecting group-free synthetic entry to the fischerindole and hapalindole indole alkaloid family has been achieved from carvone and indole. Total syntheses of (+)-hapalindole Q and (-)-12-epi-fischerindole U isothiocyanate are reported. The absolute stereochemistry of the latter natural product has also been determined.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Alkaloids / chemical synthesis*
Cyclohexane Monoterpenes
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Monoterpenes
Stereoisomerism
Terpenes / chemistry

Substances

Aldehydes
Alkaloids
Cyclohexane Monoterpenes
Indoles
Monoterpenes
Terpenes
fischerindole
hapalindole Q
carvone
indole