A bicyclo[3.2.0]hept-3-en-6-one approach to prostaglandin intermediates

E Marotta; P Righi; G Rosini

doi:10.1021/ol006664v

A bicyclo[3.2.0]hept-3-en-6-one approach to prostaglandin intermediates

Org Lett. 2000 Dec 28;2(26):4145-8. doi: 10.1021/ol006664v.

Authors

E Marotta¹, P Righi, G Rosini

Affiliation

¹ Dipartimento di Chimica Organica A. Mangini dell'Università di Bologna, Viale Risorgimento no. 4, 40136 Bologna, Italy.

PMID: 11150185
DOI: 10.1021/ol006664v

Abstract

[reaction:see text] The substituted cyclopentanic structures, 6-benzyloxymethyl-7-hydroxy-2-oxabicyclo [3.3.0]octan-3-one (1), a Corey lactone derivative, and 6-exo-benzyloxymethyl-2-oxabicyclo[3.3. 0]oct-7-en-3-one (2), have been obtained stereoselectively through the bicyclo[3.2.0]hept-3-en-6-one approach via 5-benzyloxymethyl-3-hydroxy-6-heptenoic acid, easily accessible from the inexpensive monoprotected cis-2-butene-1,4-diol.

Publication types

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

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Molecular Structure
Prostaglandins / chemistry*

Substances

Bridged Bicyclo Compounds, Heterocyclic
Prostaglandins
bicyclo(3,2,o)hept-3-en-6-one