Crystal structure of doisynolic acid and the structure of other products formed during its synthesis.
The crystal structure of the D-seco-estrogen doisynolic acid shows it to have the natural S configuration at the position derived from C-14 in estrone. Two major by-products during the synthesis of doisynolic acid from estrone are shown to be dimeric steroids. One is an aldol condensation product, and the other appears to arise from an alkaline cleavage of the aldol product.
Chi
D Y
DY
Department of Chemistry, University of Illinois, Urbana 61801, USA.
Wilson
S R
SR
Katzenellenbogen
J A
JA
D003460:Crystallization; D018360:Crystallography, X-Ray; D004963:Estrenes / Q000138:chemical synthesis / Q000737:chemistry*; D004970:Estrone / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D006878:Hydroxides; D046911:Macromolecular Substances; D008968:Molecular Conformation; D015394:Molecular Structure; D017680:Potassium Compounds; D012632:Secosteroids / Q000138:chemical synthesis / Q000737:chemistry*
D004963:Estrenes; D006878:Hydroxides; D046911:Macromolecular Substances; D017680:Potassium Compounds; D012632:Secosteroids; D004970:Estrone; C003595:doisynolic acid; C029943:potassium hydroxide