Model study for steroidal D/C ring closure in olefinic cyclization reactions; a MINDO/3 study

A. Corvers, P.C.H. Scheers, W.A.M. Castenmiller, H.M. Buck

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)

Abstract

MINDO/3 molecular orbital calculations are performed for the ring closure of (Z)- and (E)-allkenes as a model for the D/C ring closure to steroids. It is shown that a lower activation energy is needed for cyclizations in the chair configuration, than for cyclizations in the boat configuration. An analogous picture is found by comparison of (E)- and (Z)-alkenes. Cyclization of the (E)-alkene in the chair or boat configuration is energetically favoured over the ring closure of (Z)-alkenes. These results are in agreement with the Stork-Eschenmoser hypothesis.
Original languageEnglish
Pages (from-to)457-459
Number of pages3
JournalTetrahedron
Volume34
Issue number4
DOIs
Publication statusPublished - 1978

Fingerprint Dive into the research topics of 'Model study for steroidal D/C ring closure in olefinic cyclization reactions; a MINDO/3 study'. Together they form a unique fingerprint.

Cite this