A new, practical synthesis of 2-methoxyestradiols.
An efficient and practical approach to synthesize moderate to large amounts of 2-methoxyestradiol (2-ME2) is described. The key step in the synthesis is the regioselective introduction of an acetyl group at the C-2 position of estradiol using a zirconium tetrachloride mediated Fries rearrangement carried out on estradiol diacetate. The seven step synthetic procedure readily gave 2-ME2 in 49% overall yield. Application of this method to the synthesis of 2-methoxy-7 alpha-methylestradiol is also described.
Rao
Pemmaraju N
PN
Department of Organic Chemistry, Southwest Foundation for Biomedical Research, P O Box 760549, 7620 N W Loop 410 (at Military Drive), San Antonio, TX 78227-5301, USA. pnrao@icarus.sfbr.org
Cessac
James W
JW
D000077584:2-Methoxyestradiol; D004958:Estradiol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D045166:Estradiol Congeners / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure
C477267:2-methoxy-7alpha-methylestradiol; D045166:Estradiol Congeners; D004958:Estradiol; D000077584:2-Methoxyestradiol