A STEREODIVERGENT SYNTHESIS OF (+ -)-CYCLOPHELLITOL AND (1R-ASTERISK,6S-ASTERISK)-CYCLOPHELLITOL FROM THE 7-OXABICYCLO[2.2.1]HEPT-5-ENE-2-ENDO-CARBOXYLIC ACID/

Authors
ACENA JL DEALBA E ARJONA O PLUMET J
Citation
Jl. Acena et al., A STEREODIVERGENT SYNTHESIS OF (+ -)-CYCLOPHELLITOL AND (1R-ASTERISK,6S-ASTERISK)-CYCLOPHELLITOL FROM THE 7-OXABICYCLO[2.2.1]HEPT-5-ENE-2-ENDO-CARBOXYLIC ACID/, Tetrahedron letters, 37(17), 1996, pp. 3043-3044
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
17
Year of publication
1996
Pages
3043 - 3044
Database
ISI
SICI code
0040-4039(1996)37:17<3043:ASSO(->2.0.ZU;2-I
Abstract
A concise, stereodivergent synthesis of (+/-)-cyclophellitol 1 and its unnatural diastereoisomer (1R,6S*)-cyclopbellitol 2 starting from th e Diels-Alder adduct of furan and acrylic acid is reported. The stereo chemistry of the key step (the epoxidation of alkene 3) is controlled by the nature of the hydroxyl protecting groups. (C) 1996 Elsevier Sci ence Ltd.