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Total Synthesis of [3aS-(3aα,9aα,9bβ)]-3a,4,5,9,9a,9b-Hexahydro-3a,6-dimethyl-1H-benz[e]indene-3,7(2H,8H)-dione and Derivatives, Building Blocks for the Synthesis of Glucocorticoids

✍ Scribed by Daniewski, Andrzej Robert ;Piotrowska, Emilia ;Wojciechowska, Wanda

Publisher: John Wiley and Sons
Year: 1989
Tongue: English
Weight: 417 KB
Volume: 1989
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198919890268

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✦ Synopsis

The natural and synthetic glucocorticoids are very important compounds commonly used as drugs against many diseases. Recently, we have reported the synthesis of some of the title compounds and their transformations into 6-methyl-5-androstene-3,11,17-trione 3-ethyleneacctal, a building block for the anti-inflammatory drug 6a-methylprednisolone. We now present a shorter synthesis of the tricyclic systems (title compounds), which can be converted into glucocorticoids and, as reported by Nedelec at aL2), can also be used as antiandrogens. We have also reported3) a stereoselective reductive addition of the hydride anion and some electrophiles to the enedione 1, mediated by tert-bu-L J

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