An Expeditious Total Synthesis of (±)-Sempervirol, (±)-Sugiol and (±)-Xanthopherol Methyl Ether by Acid-Catalyzed Cyclialkylation Route

References

• Banik , B. K. , Chakraborti , A. K. and Ghatak , U. R. 1986 . J. Chem. Res(S) , : 406 (M); 1986, 3391
   Google Scholar
• Banik , B. K. , Ghosh , S. and Ghatak , U. R. 1988 . Tetrahedron , in press
   Google Scholar
• Axon , B. W. , Davis , B. R. and Woodgate , P. D. 1981 . J. Chem. Soc. Perkin Trans. 1 , : 2956
   Google Scholar
• Ireland , R. E. , Baldwin , S. W. and Welch , S. C. 1972 . J. Am. Chem. Soc. , 94 : 2056
   Google Scholar
• Davis , B. R. , Hinds , M. C. and Johnson , S. J. 1985 . Aust. J. Chem. , 38 : 1815 and references cited therein
   Web of Science ®Google Scholar
• Banik , B. K. , Ghosh , S. and Ghatak , U. R. 1988 . Indian J. Chem. , 26B : 103
   Google Scholar
• Matsumoto , T. and Usui , S. 1979 . Bull. Chem. Soc. Japan , 52 : 212 For earlier syntheses see:
   Google Scholar
• Matsumoto , T. , Usui , S. and Fukui , K. 1976 . Chemistry Lett. , : 241
   Google Scholar
• Matsumoto , T. , Imai , S. , Matsubayashi , T. , Tsunenaga , F. and Fukui , K. 1972 . Chemistry Lett. , : 1159
   Google Scholar
• Ghatak , U. R. and Chatterjee , N. R. 1967 . Tetrahedron Lett. , : 4783
   Google Scholar
• Mangoni , L. and Caputo , R. 1967 . Tetrahedron Lett. , : 673
   Google Scholar
• Banerjee , A. K. and de Carrasco , M. C. S. 1986 . J. Chem. Soc. Perkin Trans. 1 , : 25 For earlier syntheses see:
   Google Scholar
• Matsumoto , T. , Usui , S. and Morimote , T. 1977 . Bull. Chem. Soc., Japan , 50 : 1575
   Web of Science ®Google Scholar
• Meyer , W. L. , Clemans , G. B. and Manning , R. A. 1975 . J. Org. Chem. , 40 : 3686
   Web of Science ®Google Scholar
• Nasipuri , D. and Guha , M. 1962 . J. Chem. Soc. , : 4248
   Google Scholar
• Bhattacharyya , S. , Ghoshal , M. and Mukherjee , D. 1987 . Tetrahedron Lett. , 28 : 2431 For earlier syntheses see
   Web of Science ®Google Scholar
• Wolinsky , J. , Lau , R. , Hamsher , J. J. and Cimarusti , C. M. 1972 . Synth. Comun. , 2 : 327
   Google Scholar
• Nasipuri , D. and Guha , M. 1962 . J. Chem. Soc. , : 4248
   Google Scholar
• Sharma , M. , Ghatak , U. R. and Dutta , P. C. 1963 . Tetrahedron , 19 : 985
   Google Scholar
• Ghatak , U. R. , Alam , S. K. and Ray , J. K. 1978 . J. Org. Chem. , 43 : 4598
   Web of Science ®Google Scholar
• Nasipuri , D. , Mitra , K. and Venkataraman , S. 1972 . J. Chem. Soc. Perkin Trans. 1 , : 1836
   Google Scholar
• White , J. D. and Sung , W. L. 1974 . J. Org. Chem. , 39 : 2323
   Google Scholar
• Roy , S. C. , Satyanarayana , G. O. S. V. and Ghatak , U. R. 1982 . J. Org. Chem. , 47 : 5361
   Google Scholar
• Fetizon , M. and Moreau , G. 1965 . Bull. Soc. Chim. Fr. , : 3479
   Google Scholar
• In contrast, in a direct synthesis (±)-sempervirol methyl ether, the AlCl3-catalyzed cyclization of 2-(2-p-iso-propyl-m-methoxyphenylethyl-1,1,3-trimethylcyclohex-3-ene gave the corresponding trans-and the cis-products (2, R1 = i-Pr; R2 = OMe) and (3, R1 = i-Pr; R2 = OMe) in 38% and 48% yields respectively (ref. 6a)
   Google Scholar
• Tori , S. , Uneyama , K. and Hamada , K. 1977 . Bull. Chem. Soc. Japan , 50 : 2503 H2SO4-AcOH (1:9) catalyzed cyclization of 2-(2-m-isopropyl-p-methoxyphenylethyl)-1, 1,3-trimethyl-cyclohex-2-ene gave the mixture of the trans-and cis-products (2, R1 = OMe, R2 = i-Pr) and (3, R1 = OMe; R2 = i-Pr) in a ratio of 40:60
   Google Scholar
• Wenkert , E. and Jackson , B. G. 1958 . J. Am. Chem. Soc. , 80 : 211
   Google Scholar
• Ghatak , U. R. , Datta , D. K. and Ray , S. C. 1960 . J. Am. Chem. Soc. , 82 : 1728
   Google Scholar
• Sengupta , P. , Choudhuri , S. N. and Khastgir , H. N. 1960 . Tetrahedron , 10 : 45
   Web of Science ®Google Scholar
• Slater , S. N. 1941 . J. Chem. Soc. , : 68
   Google Scholar