FORMAL TOTAL SYNTHESIS OF TRICHODIENE VIA SKELETAL REARRANGEMENT OF REGIOSELECTIVE PHOTOCHEMICAL [2-CYCLOADDUCTS FROM CYCLOHEXENE DERIVATIVES(2])

Authors
KITANO Y FUKUDA J CHIBA K TADA M
Citation
Y. Kitano et al., FORMAL TOTAL SYNTHESIS OF TRICHODIENE VIA SKELETAL REARRANGEMENT OF REGIOSELECTIVE PHOTOCHEMICAL [2-CYCLOADDUCTS FROM CYCLOHEXENE DERIVATIVES(2]), Journal of the Chemical Society. Perkin transactions. I, (8), 1996, pp. 829-835
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
8
Year of publication
1996
Pages
829 - 835
Database
ISI
SICI code
0300-922X(1996):8<829:FTSOTV>2.0.ZU;2-M
Abstract
A formal total synthesis of trichodiene 1 is accomplished via the phot ochemical [2 + 2] cycloaddition of 3-methylcyclohex-2-enone with methy l cyclohex-1-enecarboxylate to give methyl (1 alpha,2 beta,7 beta,8 -6 -oxotricyclo[6.4.0.0(2,7)]dodecan-1-carboxylate, and its skeletal rear rangement to give a tricyclo [6.4.0.0(2,6)] dodecene derivative. Cleav age of the central five-membered ring of the tricyclo[6.4.0.0(2,6)] do decene and modification of functional groups leads to the synthesis of trichodiene 1.