Tetrahedron

Intramolecular diels-alder reaction with furan-diene: Total synthesis of (±)-11-ketotestosterone and (±)-adrenosterone

LA Van Royen, R Mijngheer, PJ De Clercq

文献索引：Royen, Luc A. Van; Mijngheer, Roelant; Clercq, Pierre J. De Tetrahedron, 1985 , vol. 41, # 20 p. 4667 - 4680

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被引用次数: 34

摘要

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 ...