A facile total synthesis of ent-17beta-estradiol and structurally related analogues.
A facile six-step synthesis (15.2% yield) of ent-17beta-estradiol from readily accessible precursors is described. The preparation of analogues with 2-alkyl substituents, double bond unsaturation in the C-ring, a cis C,D-ring fusion and modified substituents at C(17) is also reported.
Cai
Zu Yun
ZY
Department of Molecular Biology and Pharmacology, Washington University School of Medicine, Campus Box 8103, 660 S. Euclid Ave., St. Louis, MO 63110, USA.
Covey
Douglas F
DF
D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D001671:Biochemistry / Q000379:methods*; D004958:Estradiol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D008024:Ligands; D018696:Neuroprotective Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D011960:Receptors, Estrogen / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000975:Antioxidants; D008024:Ligands; D018696:Neuroprotective Agents; D011960:Receptors, Estrogen; D004958:Estradiol