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Synthesis of estra-1,3,5(10)-trien-3,15α,16α,17β-tetrol a new metabolite of estradiol

✍ Scribed by Jack Fishman; Henry Guzik

Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
162 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new metabolite derived from estradiol and considered to be exclusively fetal in origin was obtained from neonatal and pregnancy urine by Hagen et al' and Gurpide et a12. The compound contained four acylable hydroxy functions and formed an acetonide derivative. One tentative structure suggested was *1,3,5(10)_ estratrien-3,1%,1&,17!3-tetro13. In order to establish the structure of the metabolite and to provide useful quantities of material the synthesis of this interesting compound was undertaken. The osmium tatroxide oxidation of the ar,&unsaturated ketal II4 gave as the major product the trio1 IIIa, isolated as the triacetate

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