Quantum-chemical calculation as an aid in synthesis of prostaglandins, attempt of prediction of relative stability of four stereoisomeric methyl 7-hydroxy-2-oxa-3-oxobicyclo[3.3.0]octane-6-carboxylates

• Published in: Collection of Czechoslovak chemical communications Vol. 45; no. 8; pp. 2179 - 2186
• Main Authors: Kuthan, Josef, Böhm, Stanislav, Mostecký, Jiří
• Format: Journal Article
• Language: English
• Published: 1980
• ISSN: 0010-0765; 1212-6950
• DOI: 10.1135/cccc19802179

Partial optimization of conformation structure of quantum-chemical models of the stereoisomeric lactones
I
to
IV
has been carried out by the CNDO/2 method. The calculated energy characteristic and electron distributions have been used for discussion of some factors affecting retention of 5,6-
trans
-configuration in the key intermediate of prostaglandin syntheses (formula
I
) with regard to conditions of the preparative experiments.