DIRECT CONVERSION OF 1,2-DIOL INTO ALLYL SULFIDE - REGIOSELECTIVE TRANSFORMATION OF (-)-QUINIC ACID TO (-)-SHIKIMIC ACID

Authors
SHINADA T YOSHIDA Y OHFUNE Y
Citation
T. Shinada et al., DIRECT CONVERSION OF 1,2-DIOL INTO ALLYL SULFIDE - REGIOSELECTIVE TRANSFORMATION OF (-)-QUINIC ACID TO (-)-SHIKIMIC ACID, Tetrahedron letters, 39(33), 1998, pp. 6027-6028
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
33
Year of publication
1998
Pages
6027 - 6028
Database
ISI
SICI code
0040-4039(1998)39:33<6027:DCO1IA>2.0.ZU;2-5
Abstract
Exo-1,2-diols 3 and 4 were efficiently converted into the correspondin g allyl sulfides by means of tri-n-butylphosphine (Bu3P) and diphenyl disulfide (PhS)(2). This method was applied to the introduction of a c arbon-carbon double bond from diol 11 to give allyl sulfide 12 in a hi ghly regioselective manner. The allyl sulfide 12 was transformed into (-)-shikimic acid (1) in four steps. (C) 1998 Elsevier Science Ltd. Al l rights reserved.