Identification of a novel Michael acceptor group for the reversible addition of oxygen- and sulfur-based nucleophiles. Synthesis and reactivity of the 3-alkylidene-3H-indole 1-oxide function of avrainvillamide

Andrew G Myers; Seth B Herzon

doi:10.1021/ja0372006

Identification of a novel Michael acceptor group for the reversible addition of oxygen- and sulfur-based nucleophiles. Synthesis and reactivity of the 3-alkylidene-3H-indole 1-oxide function of avrainvillamide

J Am Chem Soc. 2003 Oct 8;125(40):12080-1. doi: 10.1021/ja0372006.

Authors

Andrew G Myers¹, Seth B Herzon

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. myers@chemistry.harvard.edu

PMID: 14518979
DOI: 10.1021/ja0372006

Abstract

The 3-alkylidene-3H-indole 1-oxide functional group found in the naturally occurring alkaloid avrainvillamide has been synthesized by a cross coupling-reductive condensation sequence and found to undergo reversible addition of oxygen- and sulfur-based nucleophiles.

Publication types

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

MeSH terms

Alkenes / chemistry
Indoles / chemical synthesis
Indoles / chemistry*
Methanol / chemistry*
Models, Molecular
Oxides / chemical synthesis
Oxides / chemistry*
Oxygen / chemistry
Sulfhydryl Compounds / chemistry*
Sulfur / chemistry

Substances

Alkenes
Indoles
Oxides
Sulfhydryl Compounds
avrainvillamide
Sulfur
Oxygen
Methanol