Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone

F. J. DURÁN; A. A. GHINI; H. COIRINI; G. BURTON

TETRAHEDRON

Elsevier

Lugar: Amsterdam; Año: 2006 vol. 62 p. 4762 - 4768

0040-4020

A procedure is described for the preparation of 6-thiapregnanes in five steps from pregnenolone via a 5-oxo-7-iodo-secopregnane intermediate. The 6-thiasteroid obtained was converted into 6-thia-allopregnanolone and its sulfoxide and sulfone derivatives. The trans stereochemistry at the A/Bring junction was accomplished by stereoselective reduction of an intermediate hemithioketal with triethylsilane/BF3·Et2O. The compounds synthesized are analogs of natural neurosteroids, and exhibited GABAA receptor activity comparable to allopregnanolone.