A NOVEL SYNTHESIS OF AN A-RING PRECURSOR TO 1-ALPHA-HYDROXYVITAMIN-D

Authors
DESCHRIJVER J DECLERCQ PJ
Citation
J. Deschrijver et Pj. Declercq, A NOVEL SYNTHESIS OF AN A-RING PRECURSOR TO 1-ALPHA-HYDROXYVITAMIN-D, Tetrahedron letters, 34(27), 1993, pp. 4369-4372
Citations number
44
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
27
Year of publication
1993
Pages
4369 - 4372
Database
ISI
SICI code
0040-4039(1993)34:27<4369:ANSOAA>2.0.ZU;2-J
Abstract
A novel synthesis of the known, 1alpha-hydroxyvitamin D A-ring precurs or 10, in racemic form, is described based upon (i) the stereoselectiv e cycloaddition of allene-dienophile 2 onto 3-trimethylsilyloxyfuran 1 to give 3, and (ii) the samarium iodide induced reductive opening of the oxygen bridge in 4 to yield hydroxyketone 5, as key-steps.