Tetrahedron Letters p. 3145 - 3148 (1983)
Update date:2022-08-10
Topics:
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 5a in water as a key-step.The dienophilic side chain is readily introduced starting from 2 via a sequence involving alkylation with ethyl 4-iodo-3-ethoxycrotonate, reduction and acid hydrolysis.The reduced adduct 8a, obtained in 24 percent overall yield from 2-methyl-1,3-cyclopentanedione, is converted into (+/-)-adrenosterone (16) via base-opening to 9 and further transformation to 13, the dienediolate equivalent of which is a known intermediate in corticosteroid synthesis.
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Doi:10.1039/c9ra04429a
(2019)Doi:10.1002/ejoc.202000120
(2020)Doi:10.1039/a903202i
(1999)Doi:10.1016/S0040-4039(01)94009-2
(1972)Doi:10.1002/hlca.19350180181
(1935)Doi:10.1039/c9ob00014c
(2019)