PLAP-CATALYZED HYDROLYSIS AND OPTICAL RESOLUTION - SYNTHESIS OF 4(S),(S)-4-HYDROXY-6-(2-PHENETHYL)TETRAHYDROPYRAN-2-ONE - THE UNNATURAL MEVINOLIN ANALOG

Authors
YADAV VK KAPOOR KK
Citation
Vk. Yadav et Kk. Kapoor, PLAP-CATALYZED HYDROLYSIS AND OPTICAL RESOLUTION - SYNTHESIS OF 4(S),(S)-4-HYDROXY-6-(2-PHENETHYL)TETRAHYDROPYRAN-2-ONE - THE UNNATURAL MEVINOLIN ANALOG, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 34(12), 1995, pp. 1026-1029
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry → ACNP
ISSN journal
03764699
Volume
34
Issue
12
Year of publication
1995
Pages
1026 - 1029
Database
ISI
SICI code
0376-4699(1995)34:12<1026:PHAOR->2.0.ZU;2-2
Abstract
The oxidation of 3,4-dehydro-6-(2-phenethyl)tetrahydropyran-2-one (3) by TBHP-DBU proceeds diasteroselectively to furnish a single oxirane ( 4). Cleavage of the alpha C-O bond in 4 by NaI in refluxing 2-butanone followed by acylation of the resultant hydroxy function and PLAP-cata lyzed hydrolysis, in that order, furnishes 4(S), (S)-4-hydroxy-6-(2-ph enethyl)tetrahydropyran-2-one (5) in 94% ee.