Stereoselective generation of a nonaromatic, 3, 5-dioxygenated steroidal system through tricyclization of polyene oxide

EE Van Tamelen, DG Loughhead

Index: Tamelen, E. E. van; Loughhead, D. G. Journal of the American Chemical Society, 1980 , vol. 102, # 2 p. 869 - 870

Full Text: HTML

Citation Number: 7

Abstract

Although the biogenetic-type, total synthesis of various naturally occurring polycyclic terpenoids from squalene oxide variants has been achieved,] the fabrication of traditional steroids by polycyclization of polyene oxides so far has not been realized. 2 As a preliminary assay, we have now synthesized and studied the behavior of the monocyclic epoxide (&)-l, 3 finding that-despite the considerable dissimilarity from squalene oxide and the attendant ...