PRACTICAL PREPARATION OF BICYCLO[3.2.0]HEPT-3-EN-6-ONES AND IT UTILIZATION IN STEREOSELECTIVE TOTAL SYNTHESIS OF GRANDISOL AND LINEATIN VIAA VERSATILE INTERMEDIATE

Authors
CONFALONIERI G MAROTTA E RAMA F RIGHI P ROSINI G SERRA R VENTURELLI F
Citation
G. Confalonieri et al., PRACTICAL PREPARATION OF BICYCLO[3.2.0]HEPT-3-EN-6-ONES AND IT UTILIZATION IN STEREOSELECTIVE TOTAL SYNTHESIS OF GRANDISOL AND LINEATIN VIAA VERSATILE INTERMEDIATE, Tetrahedron, 50(10), 1994, pp. 3235-3250
Citations number
60
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
10
Year of publication
1994
Pages
3235 - 3250
Database
ISI
SICI code
0040-4020(1994)50:10<3235:PPOBAI>2.0.ZU;2-Q
Abstract
New and efficient stereoselective total syntheses have been devised fo r racemic grandisol and lineatin, two important components of pheromon ic blends. They are based on the utilisation of 1,4-dimethylbicyclo[3. 2.0]hept-3-en-6-one as a pivotal intermediate. This compound, as well as other bicyclo[3.2.0]hept-3-en-6-ones, are now easily available by a practical bicyclization of the corresponding 3-hydroxy-6-alkenoic aci ds.