Ab initio and semiempirical corroboration of the observed stereoselectivity in the transannular Diels-Alder reaction leading to steroids

Article abstract of DOI:10.1016/S0040-4020(98)00600-0

Various 14-membered macrocyclic trienes underwent transannular Dieis- Alder reactions to yield tetracyclic structures that are stereoisomers of steroids. Due to the complexity of the effects at work during these reactions, a thorough molecular modeling study was carried out. Thus, some molecular mechanics, semiempirical and ab initio methods were compared and the results were finally used to rationalize the experimental results.