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

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

Source and publish data:

Tetrahedron p. 10089 - 10110 (1998)

Update date:2022-08-05

Topics:

Authors:

Couturier, Michel

Dory, Yves L.

Fortin, Daniel

Rouillard, Alain

Deslongchamps, Pierre

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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.

Full text of DOI:10.1016/S0040-4020(98)00600-0

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