SYNTHESES OF (+ -)-RAIKOVENAL, (+/-)-PRERAIKOVENAL, AND (+/-)-EPIRAIKOVENAL/

Authors
SNIDER BB LU Q
Citation
Bb. Snider et Q. Lu, SYNTHESES OF (+ -)-RAIKOVENAL, (+/-)-PRERAIKOVENAL, AND (+/-)-EPIRAIKOVENAL/, Synthetic communications, 27(9), 1997, pp. 1583-1600
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
27
Issue
9
Year of publication
1997
Pages
1583 - 1600
Database
ISI
SICI code
0039-7911(1997)27:9<1583:SO(-(A>2.0.ZU;2-A
Abstract
(+/-)-Raikovenal (1a) has been synthesized in five steps from dihydrof ilifolone (3) by two Wittig reactions. A similar sequence provides (+/ -)-preraikovenal Epiraikovenal (1b) has been prepared by photolysis of preraikovenal or by photolysis of 5 to give 4b. Lewis acid induced cy clization of enal 5 gives cyclopentylideneacetaldehyde 16 rather than bicyclo[3.2.0]heptanecarboxaldehyde 4.