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Synthesis Based on Cyclohexadienes. 5. A New Approach to the Synthesis of a-Ring Aromatic Steroids-a Formal Total Synthesis of (+/-)-Estrone

GSRS Rao, DK Banerjee, LU Devi, U Sheriff

文献索引:Rao, G. S. R. Subba; Banerjee, D. K.; Devi, L. Uma; Sheriff, Uma Australian Journal of Chemistry, 1992 , vol. 45, # 1 p. 187 - 203

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被引用次数: 9

摘要

Abstract A new strategy for the construction of A-ring aromatic steroids which resulted in the formal total synthesis of estrone is described. Thus reaction of the adduct (9), obtained from 1-methoxy-4-methylcyclohexa-1, 4-diene and acrolein, with 3-(m-methoxypheny1) propyl- magnesium bromide followed by oxidation afforded the bicyclo [2.2. 2] octene derivative (14). Acid-catalysed rearrangement of (14) followed by an intramolecular Michael addition ...