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Total synthesis of new steroids having an aromatic A ring with a 3-OH

โœ Scribed by Philippe Maurin; Malika Ibrahim-Ouali; Maurice Santelli

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
78 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A new strategy for introducing an hydroxy group at the position 3 of an aromatic A ring in a steroid, which is a key position for biological purposes, is described. This procedure has required a judicious choice of a t-butyl ether as protective group at the beginning of the synthesis, and its deprotection can be achieved in high yield in the final step.

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A synthesis of new groups of bicyclic steroids with a bicycle [3.3.1.] nonane ring A system is described. The insertion of an additional ring is performed by means of the Bichael addition of ethyl acetoacetate to 17~ -propionoxyandrosta -1.4.6-triene-3-one (1). followed by an aldol condensation of i