Steroids p. 771 - 775 (1997)
Update date:2022-08-04
Topics:
Adamczyk, Maciej
Johnson, Donald D.
Reddy, Rajarathnam E.
Alkylation of 3.17β-bis(2-trimethylsilyl)ethoxymethyl-1,3,5(10) estratriene-6-one (2) with 5-bromo-1-pentene using NaHMDS in THF afforded 3,17β-bis(2-trimethylsilyl)ethoxymethyl-7-α-(4'-pentenyl)- 1,3,5(10)estratriene-6-one (3) in excellent stereoselectivity (>95% epimeric excess). Functionalization of the side chain in compound 3 was accomplished via ozonolysis, oxidation and esterification to give 5 in 72% yield. The reduction of ester (5) using NaBH4 in MeOH afforded the corresponding 6α- hydroxy compound (6) as a single isomer in 72% yield. The hydroxyl group in 6 was removed by converting to the corresponding xanthate (7) followed by reduction rising n-Bu3SnH to afford 8 in good yield. Finally, the SEM protective groups in 8 were removed, after which the ester function was hydrolyzed with LiOH to give 7α-(3'-carboxypropyl)estradiol (10), in 10.6% overall yield from 3.
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