A key intermediate for the convenient synthesis of series of vitamin D-3 analogues with modified side chains

Authors
Fall, Y Fernandez, C Gonzalez, V Mourino, A
Citation
Y. Fall et al., A key intermediate for the convenient synthesis of series of vitamin D-3 analogues with modified side chains, TETRAHEDR L, 42(44), 2001, pp. 7815-7817
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
44
Year of publication
2001
Pages
7815 - 7817
Database
ISI
SICI code
0040-4039(20011029)42:44<7815:AKIFTC>2.0.ZU;2-P
Abstract
Tosylate 1, which features the vitamin D triene unit, was stereoselectively synthesized from commercially available starting materials. This key inter mediate undergoes a very efficient one-pot, two-step reaction with tetrabut yl ammonium fluoride to afford vitamin D analogue 2, which bears a cyclic s ide chain. Reaction of 1 with lithium aluminium hydride and removal of the silyl protecting groups affords the 22-methylated vitamin D analogue 3. (C) 2001 Elsevier Science Ltd. All rights reserved.