SYNTHESIS OF THE (+ -)-CARBOCYCLIC ANALOGS OF ASCORBIC AND ISOASCORBIC ACID/

Authors
SCHACHTNER J STACHEL HD POLBORN K
Citation
J. Schachtner et al., SYNTHESIS OF THE (+ -)-CARBOCYCLIC ANALOGS OF ASCORBIC AND ISOASCORBIC ACID/, Tetrahedron, 51(33), 1995, pp. 9005-9014
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
33
Year of publication
1995
Pages
9005 - 9014
Database
ISI
SICI code
0040-4020(1995)51:33<9005:SOT(-A>2.0.ZU;2-X
Abstract
The synthesis of compounds 2, the racemic carbocyclic analogues of asc orbic acid 1a and isoascorbic acid 1b, has been accomplished starting from the cyclopentenone 4. Benzylation followed by diastereoselective addition to tert-butyldimethylsilyloxy acetaldehyde gave rise to a mix ture of the adducts (+/-)6a and (+/-)6b. Removal of the silyl- and ter t-butyl protecting groups proceeded cleanly to furnish reductone ether s (+/-)8a and (+/-)8b, which were finally converted by catalytic hydro genation to(+/-)2a and (+/-)2b, respectively.