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Building up of the steroid skeleton
Formation of centers of asymmetry
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Abstr acetate acetylation AcOH adduct Akad aldosterone alkaline alkylation analogs aromatic ring bicyclic Birch reduction bromide carbinol carbon atoms carried catalytic hydrogenation CD fragment centers of asymmetry Chem Chim chloride cis-C/D configuration converted corresponding d-enantiomer D-homo decarboxylation dehydration derivative described in Scheme diacid dienophile diester diketone double bond enabled enantiomer enol epimer epimeric equilenin estrone formation of ring formed gave a mixture Grignard hydrolysis hydroxy hydroxy group I. N. Nazarov intramolecular introduction isomer isomerization ketal keto acid keto ester keto group Khim lactone latter leads MeO MeO MeOH MeONa method of synthesis methyl ether Michael reaction Miescher natural steroids Nauk SSSR nonaromatic obtained over-all yield oxidation racemic Reformatskii reaction route saponification side chain sodium starting material stereochemistry steroid steroid compounds steroid skeleton structure subsequent substituents synthesis of steroids takes place tetracyclic tion total steroid synthesis total synthesis trans-C/D triketone unsaturated W. S. Johnson