UNPRECEDENTED GROB-TYPE FRAGMENTATION OF 5-DIOXOLAN-BICYCLO[4.2.0]OCTAN-2-ONES INTO 3-(METHOXYCARBONYLMETHYL)CYCLOHEXANONES

Authors
DEGIACOMO M BETTOLO RM SCARPELLI R
Citation
M. Degiacomo et al., UNPRECEDENTED GROB-TYPE FRAGMENTATION OF 5-DIOXOLAN-BICYCLO[4.2.0]OCTAN-2-ONES INTO 3-(METHOXYCARBONYLMETHYL)CYCLOHEXANONES, Tetrahedron letters, 38(19), 1997, pp. 3469-3470
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
19
Year of publication
1997
Pages
3469 - 3470
Database
ISI
SICI code
0040-4039(1997)38:19<3469:UGFO5>2.0.ZU;2-R
Abstract
The unprecedented Grob-type fragmentations of 5-dioxolan-bicyclo[4.2.0 ]octan-2-ones 1 into 3-(methoxycarbonylmethtl)cyclohexanes 2 are descr ibed. This fragmentation, in combination with the allene photoannelati on used to produce compounds 1, might constitute an indirect way for a chieving: conjugate addition of methyl acetate; new syntheses of kaura ne, stemarane and thirsiflorane diterpenes might be also envisaged fro m 2c and 2d. (C) 1997 Elsevier Science Ltd.