SYNTHESIS OF ESTRONE VIA A THALLIUM(III)-MEDIATED FRAGMENTATION OF A 19-HYDROXY-ANDROST-5-ENE PRECURSOR

Authors
KOCOVSKY P BAINES RS
Citation
P. Kocovsky et Rs. Baines, SYNTHESIS OF ESTRONE VIA A THALLIUM(III)-MEDIATED FRAGMENTATION OF A 19-HYDROXY-ANDROST-5-ENE PRECURSOR, Tetrahedron letters, 34(38), 1993, pp. 6139-6140
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
38
Year of publication
1993
Pages
6139 - 6140
Database
ISI
SICI code
0040-4039(1993)34:38<6139:SOEVAT>2.0.ZU;2-9
Abstract
Estrone (6) has been synthesized from 1, an industrial precursor of an drostane steroids, in seven steps. Key features of the strategy includ e the functionalization of C-19 (1 --> 2) and a stereoelectronically c ontrolled, Tl(III)-mediated degradation (2 --> 3). Oppenauer oxidation of diol 4 then gave the unsaturated hydroxyketone 5, acid treatment o f which induced aromatization affording 6.