Total synthesis of (+)-phomactin a using a B-alkyl Suzuki macrocyclization

Peter J Mohr; Randall L Halcomb

doi:10.1021/ja0296531

Total synthesis of (+)-phomactin a using a B-alkyl Suzuki macrocyclization

J Am Chem Soc. 2003 Feb 19;125(7):1712-3. doi: 10.1021/ja0296531.

Authors

Peter J Mohr¹, Randall L Halcomb

Affiliation

¹ Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.

PMID: 12580592
DOI: 10.1021/ja0296531

Abstract

A total synthesis of (+)-phomactin A is described using a B-alkyl Suzuki macrocyclization to incorporate the isolated trisubstituted olefin. This macrocyclization was accomplished with the sensitive hydrated furan ring in place. (R)-(+)-pulegone was used to establish the highly substituted cyclohexene core of the molecule.

Publication types

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

MeSH terms

Cyclization
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*

Substances

Heterocyclic Compounds, 4 or More Rings
phomactin A

Grants and funding

GM53496/GM/NIGMS NIH HHS/United States