Formal total synthesis of RK-397 via an asymmetric hydration and iterative allylation strategy

Haibing Guo; Matthew S Mortensen; George A O'Doherty

doi:10.1021/ol801055b

Formal total synthesis of RK-397 via an asymmetric hydration and iterative allylation strategy

Org Lett. 2008 Jul 17;10(14):3149-52. doi: 10.1021/ol801055b. Epub 2008 Jun 13.

Authors

Haibing Guo¹, Matthew S Mortensen, George A O'Doherty

Affiliation

¹ Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.

PMID: 18549226
DOI: 10.1021/ol801055b

Abstract

A formal total synthesis of the oxopentaene macrolide antibiotic RK-397 has been achieved. Nine stereocenters were established by a combination of allylation and our asymmetric hydration reactions and a 1,5 anti-selective aldol reaction. The synthesis proceeded in 19 steps from simple achiral conjugated dienoates.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Macrolides / chemical synthesis*
Macrolides / chemistry
Molecular Structure
Stereoisomerism

Substances

Anti-Bacterial Agents
Macrolides
RK 397