Synthesis of 6-thia-analogs of the natural neurosteroid allopregnanolone.

DURAN, F.J.; GHINI, A.A.; COIRINI, H.; BURTON, G.

TETRAHEDRON

Elsevier Ltd.

Lugar: Londres; 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 theA/B ring junction was accomplished by stereoselective reduction of an intermediatehemithioketalwith triethylsilane/BF3/Et2O. The compounds synthesized are analogs of natural neurosteroids, and exhibited GABAA receptor activity comparable to allopregnanolone.