Total synthesis of (±)-cylindricine C

Guillaume Lapointe; Kurt Schenk; Philippe Renaud

doi:10.1021/ol201745s

Total synthesis of (±)-cylindricine C

Org Lett. 2011 Sep 16;13(18):4774-7. doi: 10.1021/ol201745s. Epub 2011 Aug 12.

Authors

Guillaume Lapointe¹, Kurt Schenk, Philippe Renaud

Affiliation

¹ University of Bern, Department of Chemistry and Biochemistry, Freiestrasse 3, CH-3012 Bern, Switzerland.

PMID: 21838228
DOI: 10.1021/ol201745s

Abstract

A concise synthesis of (±)-cylindricine C and its C(13)-epimer is described. Starting from 1-octyne, cylindricine C and 13-epi-cylindricine C were prepared in 11% and 15% yields, respectively. The synthesis involves the preparation of the central tricyclic moiety via a radical α-iodoketone carboazidation/bis-reductive amination sequence. Inversion of the stereochemistry at C(13) and C(5) was efficiently achieved on late stage intermediates.

Publication types

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

MeSH terms

Crystallography, X-Ray
Heterocyclic Compounds, 3-Ring / chemical synthesis*
Heterocyclic Compounds, 3-Ring / chemistry
Models, Molecular
Molecular Structure
Quinolones / chemical synthesis*
Quinolones / chemistry
Stereoisomerism

Substances

Heterocyclic Compounds, 3-Ring
Quinolones
cylindricine C