Efforts toward the total synthesis of (-)-kendomycin

David R Williams; Khalida Shamim

doi:10.1021/ol051512r

Efforts toward the total synthesis of (-)-kendomycin

Org Lett. 2005 Sep 15;7(19):4161-4. doi: 10.1021/ol051512r.

Authors

David R Williams¹, Khalida Shamim

Affiliation

¹ Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, Indiana 47405, USA. williamd@indiana.edu

PMID: 16146377
DOI: 10.1021/ol051512r

Abstract

[structure: see text] The synthesis of an advanced component leading to (-)-kendomycin is described. The synthetic scheme features the application of asymmetric conjugate addition methodology for the early generation of the C13-C14 (E)-trisubstituted olefin, providing an efficient assembly of the ansa chain. Condensation reactions probe two strategies for attachment of the aromatic system.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Aldehydes / chemistry
Alkenes / chemistry
Molecular Structure
Rifabutin / analogs & derivatives*
Rifabutin / chemical synthesis
Rifabutin / chemistry

Substances

Aldehydes
Alkenes
kendomycin
Rifabutin

Grants and funding

GM-42897/GM/NIGMS NIH HHS/United States