NOVEL STEREOCONTROLLED SYNTHESIS OF THE TRICYCLIC LACTONE 9-DIMETHYL-8-OXO-7-OXATRICYCLO[4.3.0.0(3,9)]NONANE

Authors
RICO R ZAPICO J BERMEJO F SANNI SB GARCIAGRANDA S
Citation
R. Rico et al., NOVEL STEREOCONTROLLED SYNTHESIS OF THE TRICYCLIC LACTONE 9-DIMETHYL-8-OXO-7-OXATRICYCLO[4.3.0.0(3,9)]NONANE, Tetrahedron : asymmetry, 9(2), 1998, pp. 293-303
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
2
Year of publication
1998
Pages
293 - 303
Database
ISI
SICI code
0957-4166(1998)9:2<293:NSSOTT>2.0.ZU;2-#
Abstract
The stereocontrolled synthesis of 9-dimethyl-s-oxo-7-oxatricyclo[4.3.0 .0(3,9)]nonane 1 from (R)-(-)-carvone has been accomplished by applica tion of a 13-step sequence with 12% overall yield. The absolute stereo chemistry of the unsaturated acid 8a has been established by X-ray ana lysis of the chiral amide 8c. (C) 1998 Elsevier Science Ltd. All right s reserved.