Enantioselective synthesis of cyclohepta[b]indoles: gram-scale synthesis of (S)-SIRT1-inhibitor IV

Philipp J Gritsch; Erik Stempel; Tanja Gaich

doi:10.1021/ol4026217

Enantioselective synthesis of cyclohepta[b]indoles: gram-scale synthesis of (S)-SIRT1-inhibitor IV

Org Lett. 2013 Nov 1;15(21):5472-5. doi: 10.1021/ol4026217. Epub 2013 Oct 23.

Authors

Philipp J Gritsch¹, Erik Stempel, Tanja Gaich

Affiliation

¹ Institute of Organic Chemistry, Leibniz University Hannover , Schneiderberg 1, 30167 Hannover, Germany.

PMID: 24152090
DOI: 10.1021/ol4026217

Abstract

An enantioselective gram-scale synthesis of one of the most potent SIRT1-inhibitors has been accomplished by an unprecedented domino reaction sequence establishing the cyclohepta[b]indole core. This method was developed for application in natural product synthesis of a variety of indole alkaloids.

Publication types

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

MeSH terms

Biological Products
Catalysis
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Sirtuin 1 / analysis*
Sirtuin 1 / chemical synthesis*
Sirtuin 1 / chemistry
Stereoisomerism

Substances

Biological Products
Indole Alkaloids
Indoles
Sirtuin 1