Highly substituted oxabicyclic derivatives from furan: synthesis of (±)-platensimycin

E Zachary Oblak; Dennis L Wright

doi:10.1021/ol2005775

Highly substituted oxabicyclic derivatives from furan: synthesis of (±)-platensimycin

Org Lett. 2011 May 6;13(9):2263-5. doi: 10.1021/ol2005775. Epub 2011 Mar 31.

Authors

E Zachary Oblak¹, Dennis L Wright

Affiliation

¹ Department of Pharmaceutical Sciences, University of Connecticut, Storrs, Connecticut 06269, United States.

PMID: 21452821
DOI: 10.1021/ol2005775

Abstract

A stereocontrolled approach to a key platensimycin intermediate was achieved from a commercially available furylcarboxylate. Key to our approach is the highly efficient formal [4 + 3] cyclocondensation of a substituted furan with tetrabromocyclopropene along with an intramolecular γ-alkylation to construct the final ring of the caged intermediate.

Publication types

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

MeSH terms

Adamantane / chemical synthesis*
Alkylation
Aminobenzoates / chemical synthesis*
Anilides / chemical synthesis*
Anti-Bacterial Agents / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Furans / chemistry*
Molecular Structure
Oxygen Compounds / chemistry*
Stereoisomerism
Streptomyces / chemistry

Substances

Aminobenzoates
Anilides
Anti-Bacterial Agents
Bridged Bicyclo Compounds, Heterocyclic
Furans
Oxygen Compounds
Adamantane
platensimycin
furan