Tetrahedron p. 4667 - 4680 (1985)
Update date:2022-09-26
Royen, Luc A. Van
Mijngheer, Roelant
Clercq, Pierre J. De
A novel D <*> BCD <*> ABCD route to 11-keto steroids is reported involving a high yield stereoselective intramolecular Diels-Alder reaction of furan-diene 12 in water as a key-step.The dienophilic side chain is readily introduced starting from 8 via a sequence involving alkylation with ethyl (E)-3-ethoxy-4-iodo-2-butenoate, reduction and acid hydrolysis.The reduced adduct 14 is further converted into (+/-)-adrenosterone (6) via 24, the dienediolate equivalent of which is a known intermediate in corticosteroid synthesis.
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Doi:10.1081/NCN-200060271
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