Studies on the syntheses of benzoquinone ansamycin antibiotics. Syntheses of the C5-C15 subunits of macbecin I, geldanamycin, and herbimycin A

Justin K Belardi; Glenn C Micalizio

doi:10.1021/ol0607995

Studies on the syntheses of benzoquinone ansamycin antibiotics. Syntheses of the C5-C15 subunits of macbecin I, geldanamycin, and herbimycin A

Org Lett. 2006 May 25;8(11):2409-12. doi: 10.1021/ol0607995.

Authors

Justin K Belardi¹, Glenn C Micalizio

Affiliation

¹ Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.

PMID: 16706538
DOI: 10.1021/ol0607995

Abstract

[reaction: see text] A general and convergent route to the C(5)-C(15) subunits of the benzoquinone ansamycin antibiotics macbecin I, geldanamycin, and herbimycin A is described. Each subunit is prepared by the stepwise coupling of differentially functionalized aldehydes with a pentenyl dianion equivalent derived from diastereoselective pentynylation and regioselective reductive coupling.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Benzoquinones / chemical synthesis*
Benzoquinones / chemistry*
Lactams, Macrocyclic / chemical synthesis*
Molecular Structure
Rifabutin / analogs & derivatives
Stereoisomerism

Substances

Anti-Bacterial Agents
Benzoquinones
Lactams, Macrocyclic
Rifabutin
quinone
herbimycin
macbecin I
geldanamycin