A bicyclo[3.2.0]hept-3-en-6-one approach to prostaglandin intermediates.
[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.
Marotta
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Dipartimento di Chimica Organica A. Mangini dell'Università di Bologna, Viale Risorgimento no. 4, 40136 Bologna, Italy.
Righi
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Rosini
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D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D015394:Molecular Structure; D011453:Prostaglandins / Q000737:chemistry*
D019086:Bridged Bicyclo Compounds, Heterocyclic; D011453:Prostaglandins; C419322:bicyclo(3,2,o)hept-3-en-6-one