Efficient synthesis of (+/-)-, (+)-, and (-)-conduritol C via palladium(II)-catalyzed 1,4,-diacetoxylation in combination with enzymatic hydrolysis

Authors
Yoshizaki, H Backvall, JE
Citation
H. Yoshizaki et Je. Backvall, Efficient synthesis of (+/-)-, (+)-, and (-)-conduritol C via palladium(II)-catalyzed 1,4,-diacetoxylation in combination with enzymatic hydrolysis, J ORG CHEM, 63(25), 1998, pp. 9339-9341
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
63
Issue
25
Year of publication
1998
Pages
9339 - 9341
Database
ISI
SICI code
0022-3263(199812)63:25<9339:ESO((A>2.0.ZU;2-H
Abstract
Palladium-catalyzed diacetoxylation of 5,6-isopropylendioxy-1,3-cyclohexadi ene (3) was stereoselective and gave the trans-diacetate 4 (>94% trans), wh ich after hydrolysis and deprotection, afforded (+/-)-conduritol. Enzymatic hydrolysis of diacetate 4 produced enantiomerically pure diol (-)-5 (>99.5 % ee) and enantiomerically pure (+)-4 (>99.5% ee). Compounds (-)-5 and (1)- 4 were subsequently transformed to (-)- and (+)-conduritol C, respectively.