Total synthesis of the ethyl ester of the major urinary metabolite of prostaglandin E(2)

Douglass F Taber; Dawei Teng

doi:10.1021/jo011017i

Total synthesis of the ethyl ester of the major urinary metabolite of prostaglandin E(2)

J Org Chem. 2002 Mar 8;67(5):1607-12. doi: 10.1021/jo011017i.

Authors

Douglass F Taber¹, Dawei Teng

Affiliation

¹ Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberd@udel.edu

PMID: 11871893
DOI: 10.1021/jo011017i

Abstract

The preparation of the ethyl ester of the major urinary metabolite of prostaglandin E(2) 3 is described. The key step is the kinetic opening of the TBS-protected bicyclic ketone 7 with thiophenol.

MeSH terms

Chemistry, Organic / methods
Dinoprostone / analogs & derivatives*
Dinoprostone / chemical synthesis*
Dinoprostone / chemistry
Dinoprostone / urine
Esters / chemical synthesis
Esters / chemistry
Ethane / analogs & derivatives
Ethane / chemical synthesis
Ethane / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism

Substances

Esters
Dinoprostone
Ethane