A new and short enantioselective synthesis of (R)-pantolactone

Authors
Upadhya, TT Gurunath, S Sudalai, A
Citation
Tt. Upadhya et al., A new and short enantioselective synthesis of (R)-pantolactone, TETRAHEDR-A, 10(15), 1999, pp. 2899-2904
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
15
Year of publication
1999
Pages
2899 - 2904
Database
ISI
SICI code
0957-4166(19990730)10:15<2899:ANASES>2.0.ZU;2-Q
Abstract
Dihydro-4,4-dimethyl-2(3H)-furanone 6, the key intermediate to (R)-pantolac tone 2, has been synthesized in two steps via the radical cyclization of br omoether 5. Silyl enol ether 7, prepared from 6, on Sharpless asymmetric di hydroxylation gave (R)-pantolactone 2 in moderate yield and excellent enant ioselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.