4613-37-0Relevant academic research and scientific papers
Synthesis of Methyl Substituted Bicyclohept-3-en-6-ones and 3,3a,4,6a-Tetrahydro-2H-cyclopentafuran-2-ones.
Marotta, Emanuela,Pagani, Ilaria,Righi, Paolo,Rosini, Goffredo
, p. 7645 - 7656 (2007/10/02)
Treatment of methyl mono- or bisubstituted 3-hydroxy-6-alkenoic acids in acetic anhydride and potassium acetate give the corresponding bicyclohept-3-en-6-ones in fair to good yields.This reaction appears to be of general applicability to prepare the methyl derivatives in all the positions of the five membered ring.The synthesis of 4,7,7-trimethylbicyclohept-3-en-6-one (filifolone) by an efficient bicyclization of 3-hydroxy-3-methyl-6-heptenoic acid followed by the geminal dimethylation of the intermediate 4-methylbicyclohept-3-en-6-one is reported.The latter reaction proved to be a general method when performed on bicyclohept-3-en-6-ones and on bicyclohept-2-en-6-one. 3,3a,4,6a-Tetrahydro-2H-cyclopentafuran-2-ones, important starting materials in the synthesis of linear condensed triquinane sesquiterpenes, have been prepared in an efficient manner by the easy bicyclization of 3-hydroxy-6-heptenoic acids, followed by a Baeyer-Villiger oxidation of the bicyclohept-3-en-6-one intermediates.
Terpenes and Terpene Derivatives, XVII. - Thermal and AlCl3-Catalyzed Reaction of Ocimenone
Weyerstahl, Peter,Zombik, Winfried,Gansau, Christian
, p. 422 - 427 (2007/10/02)
Bis(trans-ocimenone) (5),reported to be a naturally occuring compound, is formed by thermal dimerization of (E)-ocimenone (E-4). - Treatment of 4 with AlCl3 leads, in addition to unchanged 4, to a mixture of the rearranged products filifolone (6) and rac-
TOTAL SYNTHESIS OF (+-)-FILIFOLONE
Hudlicky, T.,Kutchan, T.
, p. 691 - 692 (2007/10/02)
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.
