CONVENIENT SYNTHESIS OF 1-ALPHA,25-DIHYROXYVITAMIN-D3 FROM VITAMIN-D2

Authors
TAKAHASHI M SAKAKIBARA Y
Citation
M. Takahashi et Y. Sakakibara, CONVENIENT SYNTHESIS OF 1-ALPHA,25-DIHYROXYVITAMIN-D3 FROM VITAMIN-D2, Bulletin of the Chemical Society of Japan, 67(9), 1994, pp. 2494-2499
Citations number
23
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
67
Issue
9
Year of publication
1994
Pages
2494 - 2499
Database
ISI
SICI code
0009-2673(1994)67:9<2494:CSO1FV>2.0.ZU;2-J
Abstract
toxy-6-(1,3-benzodithiol-2-yloxy)-3,5-cyclovitamin D2 (7) was synthesi zed from vitamin D2 by five steps. The new compound 7 was ozonized reg ioselectively and subsequently reduced, leading to (7E)-(1S,3S, yclo-9 ,10-seco23,24-dinor-7,10(19)-choladien-22-ol (11). The alcohol 11 obta ined as a key intermediate was tosylated, iodinated, and coupled with yl-4-phenylsulfonyl-2-(tetrahydropyranyloxy)butane to give lsulfonyl-2 5-tetrahydropyranyloxy-3,5-cyclovitamin D3 (16). By desulfonylation an d hydrolysis of the compound 16 1alpha,25-dihydoxyvitamin D3 was obtai ned selectively.