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
(2005)Doi:10.1021/acs.orglett.9b02592
(2019)Doi:10.1021/ja00313a029
(1984)Doi:10.3109/14756366.2011.645241
(2013)Doi:10.1002/hlca.19830660516
(1983)Doi:10.1007/s10593-005-0125-4
(2005)
