6570-44-1Relevant academic research and scientific papers
Synthesis Based on Cyclohexadienes. V. A New Approach to the Synthesis of A-Ring Aromatic Steroids: a Formal Total Synthesis of (+/-)-Estrone
Rao, G. S. R. Subba,Banerjee, D. K.,Devi, L. Uma,Sheriff, Uma
, p. 187 - 203 (2007/10/02)
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-methoxyphenyl
Conformational deformation of ring C in 14β-estra-1,3,5(10),15-tetraen-17-ones
Bull,Dillen,Sefton
, p. 8143 - 8152 (2007/10/02)
High-field n.m.r. analysis of four 3-methoxy-14β-estra-1,3,5(10),15-tetraen-17-ones provides evidence for conformational deformation of ring C to a twist-boat form in solution. These observations are supported by molecular mechanics (MM2) calculations, which predict that the ring C chair and ring C twist-boat conformers have similar steric energies, slightly favouring the latter. An X-ray crystal structure determination on 3-methoxy-14-methyl-14β-estra-1,3,5(10)-,15-tetraen-17-one revealed that ring C does indeed adopt a twist-boat conformation in the solid state.
