@article{8b061e9b4c11411596d096b2ae34f76f,
title = "Total synthesis of (±)-filifolone.",
abstract = "Monoterpene filifolone has been synthesized by an intramolecular acid catalyzed alkylation of dienic diazoketone. The potential utility of the key transformation in the synthesis of a new terpene synthon is indicated.",
author = "T. Hudlicky and T. Kutchan",
note = "Funding Information: the substitution of the olefin and thereby on the reactivity of the corresponding cation. Ketone Lwas isomerized to filifolone 1 12 by treatment with RhCl3 in aqueous ethanol13 in 30-40% yield and proved spectrally identical to the natural product. In view of its accessibility and of its troublesome isomerization it would seem that 1 is far better suited for the conversion to cyclopentane gthan filifolone itself. It appears likely that once the ring strain experienced in 1 is removed by cleavage of the cyclobutanone, isomerization becomes more feasible and with it the possibility of invoking greater stereo-selectivity in generating 2. The oxidative conversion of gto 3 in which the necessary stereochemical demands of acorane sesquiterpenes have been met, is presently being investigated, Acknowledgements: The authors wish to thank the donors of Petroleum Research Fund administered by the American Chemical Society. Thanks are extended to Dr. J. Hudson, University of Texas, for determination of mass spectral measurements and to Professor R. Bates, University of Arizona for providing the spectra and derivatives of filifolone.",
year = "1980",
doi = "10.1016/S0040-4039(00)71447-X",
language = "English",
volume = "21",
pages = "691--692",
journal = "Tetrahedron Letters",
issn = "0040-4039",
number = "8",
}