A Convenient Synthesis of 2,2,4-Trimethylcyclohexane-1,3-Dione: A Useful Precursor for The Taxoid a Ring

References

• Wani , M. C. , Taylor , H. L. , Wall , M. E. , Coggon , P. and McPhail , A. T. 1971 . J. Am. Chem. Soc. , 93 : 2325 Georg, G. I.; Chen, T. T.; Ojima, I.; Vyas, D. M., Eds.; ACS Symposium Series 583, “Taxane Anticancer Agents: Basic Science and Current Status,” American Chemical Society, Washington D. C., 1995. Suffness, M. Ed.; “Taxol: Science and Applications,” CRC Press, New York, 1995. Guenard, D.; Gueritte-Voegelein, F.; Potier, P. Acc. Chem. Res., 1993, 26, 160, and references cited therein.
   PubMed Web of Science ®Google Scholar
• For total syntheses of taxol: Nicolaou K. C. Yang Z. Liu J. J. Ueno H. Nantermet P. G. Claiborne C. F. Renaud J. Couladouros E. A. Paulvannan K. Sorensen E. J. Nature 1994 367 630
   PubMed Web of Science ®Google Scholar
• Holton , R. A. , Somoza , C. , Kim , H. B. , Liang , F. , Biediger , R. J. , Boatman , P. D. , Shindo , M. , Smith , C. C. , Kim , S. , Nadizadeh , H. , Suzuki , Y. , Tao , C. , Vu , P. , Tang , S. , Zhang , P. , Murthi , K. K. , Gentile , L. N. and Liu , J. H. 1994 . J. Am. Chem. Soc. , 116 : 1599
   Web of Science ®Google Scholar
• Masters , J. J. , Link , J. T. , Synder , L. B. , Young , W. B. and Danishefsky , S. 1995 . Angew. Chem. Int. Ed. Engl. , 34 : 1723
   Web of Science ®Google Scholar
• Wender , P. A. , Badham , N. F. , Conway , S. P. , Floreancig , P. E. , Glass , T. E. , Houze , J. B. , Krauss , N. E. , Lee , D. , Marquess , D. G. , McGrane , P. L. , Meng , W. , Natchus , M. G. , Shuker , A. J. , Sutton , J. C. and Taylor , R. E. 1997 . J. Am. Chem. Soc. , 119 : 2757
   Web of Science ®Google Scholar
• For reviews on synthetic approaches to taxol systems: Nicolaou K. C. Dai W.-M. Guy R. K. Angew. Chem., Int. Ed. Engl. 1994 33 15
   Web of Science ®Google Scholar
• Boa , A. N. , Jenkins , P. R. and Nawrence , N. J. 1994 . Contemp. Org. Synth. , 1 : 47
   Google Scholar
• Kingston , D. G. I. , Molinero , A. A. and Rimoldi , J. M. 1993 . Prog. Chem. Org. Nat. Prod. , 61 : 1
   Google Scholar
• Swindell , C. S. 1993 . Stud. Nat. Prod. Chem. , 12 : 179
   Google Scholar
• Paquette , L. A. 1992 . Stud. Nat. Prod. Chem. , 11 : 3
   Google Scholar
• Kingston , D. G. I. 1991 . Pharmac. Ther. , 52 : 1
   PubMed Web of Science ®Google Scholar
• Swindell , C. S. 1991 . Org. Prep. Proced. Int. , 23 : 465
   Web of Science ®Google Scholar
• Detering , J. and Martin , H.-D. 1988 . Angew. Chem. Int. Ed. Engl. , 27 : 695
   Google Scholar
• Queneau , Y. , Krol , W. J. , Bornmann , W. G. and Danishefsky , J. 1992 . J. Org. Chem. , 57 : 4043
   Google Scholar
• De Grandi , M. J. , Jung , D. K. , Krol , W. J. and Danishefksy , S. J. 1993 . J. Org. Chem. , 58 : 4989
   Google Scholar
• Young , W. B. , Masters , J. J. and Danishefsky , S. 1995 . J. Am. Chem. Soc. , 117 : 5228
   Google Scholar
• Masters , J. J. , Jung , D. K. , Danishefsky , S. J. , Synder , L. B. , Park , T. K. , Isaacs , R. C. A. , Alaimo , C. A. and Young , W. B. 1995 . Angew. Chem. Int. Ed. Engl. , 34 : 452
   Google Scholar
• Montalbetti , C. , Savignac , M. , Bonnefis , F. and Genet , J. P. 1995 . Tetrahedron Letts. , 36 : 5891
   Google Scholar
• Danishefsky , S. J. , Masters , J. J. , Young , W. B. , Link , J. T. , Synder , L. B. , Magee , T. V. , Jung , D. K. , Isaacs , R. C. A. , Bornmann , W. G. , Alaimo , C. A. , Coburn , C. A. and Di Grandi , M. J. 1996 . J. Am. Chem. Soc. , 118 : 2843
   Web of Science ®Google Scholar
• Swindell , C. S. and Fan , W. 1996 . Tetrahedron Letts. , 37 : 2321
   Web of Science ®Google Scholar
• Swindell , C. S. , Chander , M. C. , Heerding , J. M. , Klimko , P. G. , Rahman , L. T. , Raman , J. V. and Venkataraman , H. 1996 . J. Org. Chem. , 61 : 1101
   Google Scholar
• Swindell , C. S. and Fan , W. 1996 . J. Org. Chem. , 61 : 1109
   Google Scholar
• Delaloge , F. , Prunet , J. , Pancrazi , A. and Lallemand , J-Y. 1997 . Tetrahedron Letts. , 38 : 237
   Google Scholar
• Hargreaves , J. R. , Hickmott , P. W. and Hopkins , B. J. 1968 . J. Chem. Soc. (C) , : 2599
   Google Scholar
• Baumann , M. and Hoffmann , W. Ger. Offen. . DE 3,112,056 . Chem. Abstr. 1983, 98: 34307u.
   Google Scholar
• For other methods to 7: Via reaction of 3-morpholinopent-2-ene with acryloyl chloride see ref. 6.
   Google Scholar
• Methylation of enolate derived from 2-methyl-3-(1-pyrrolidyl)-2-cyclohexen-1-one: Telschow J. E. Reusch W. J. Org. Chem. 1975 40 862
   Google Scholar
• Methylation of 3-iso-butoxy-2-methyl-2-cyclohexene-1-one: Piers E. Grierson J. R. Lau C. K. Nagakura I. Can. J. Chem. 1982 60 210 Muskopf, J. W.; Coates, R. M. J. Org. Chem. 1985 50, 69
   Google Scholar
• Via cyclization: Vakulova L. A. Fokina L. N. Mishchenko V. V. Filippova T. M. Dzhiembaev B. Zh. Starostina A. K. Yakovieva I. M. Samokhvalov G. I. Zhurnal Obshchei Khimii 1975 45 2499 Schaafsma, S. E.; Claassens, J. E. L.; Verheijen, E. J. M. Ger. Offen., 1974, 2,412,313; Chem. Abstr., 1975, 82, 3861k; Mueller, W. H.; Hey, H.; Meidert, H. Ger. Offen., 1976, 2,448,677; Chem. Abstr., 1976, 85, 32524v.
   Google Scholar