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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 22
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Original Articles

Termite Trail Attractants: New Syntheses of Racemic (E)-α-, (Z)-α- and β-Bisabolenes

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Pages 3167-3188 | Received 20 Apr 1994, Published online: 23 Sep 2006

References

  • Work supported by the Consiglio Nazionale delle Ricerche (CNR, Roma), Progetto Strategico Beni Culturali, and by the Ministero dell' Università e della Ricerca Scientifica e Tecnologica (MURST).
  • Argenti , L. , Bellina , F. , Carpita , A. , Rossi , E. and Rossi , R. Synth. Commun. , accepted for publication.
  • Klochov , S. G. , Kozlovskii , V. I. and Pushin , A. N. 1989 . Khim. Prir. Soedin. , : 416
  • 1989 . Chem. Abstr. , 111 : 93946m
  • Horvath , R. F. and Chan , T. H. 1989 . J. Org. Chem. , 54 : 317
  • Baldwin , J. E. , Adlington , R. M. , Ichikawa , Y. and Kneale , C. J. 1988 . J. Chem. Soc. Chem. Commun. , : 702
  • Delay , F. and Ohloff , G. 1979 . Helv. Chim. Acta , 62 : 369
  • Giraudi , E. , Plattier , M. and Teisseire , P. 1974 . Recherches , 19 : 205
  • Becker , M. and Weyersthal , P. 1979 . Helv. Chim. Acta , 62 : 2724
  • Cahiez , G. , Rivas-Enterrios , J. and Clery , P. 1988 . Tetrahedron Lett. , 29 : 3659
  • Kuehne , M. E. and Horne , D. A. 1975 . J. Org. Chem. , 40 : 1287
  • Corey , E. J. and Suggs , J. W. 1975 . Tetrahedron Lett. , : 2647
  • Corey , E. J. and Fuchs , P. L. 1972 . Tetrahedron Lett. , : 3769
  • Bellina , F. , Carpita , A. , Adorni Fontana , E. and Rossi , R. Tetrahedron , in press.
  • DelValle , L. , Stille , J. K. and Hegedus , L. S. 1990 . J. Org. Chem. , 55 : 3019
  • Aldrich , J. R. , Numata , H. , Borges , M. , Bin , F. , Waite , G. K. and Lusby , W. R. 1993 . Z. Naturforsch. , 48c : 73
  • Numata , H. 1990 . Shokubutsu Boeki , 44 : 308
  • 1991 . Chem. Abstr. , 114 : 2117q
  • Buss , A. D. , Greeves , N. , Mason , R. and Warren , S. 1987 . J. Chem. Soc. Perkin Trans I , : 2569
  • Vig , O. P. and Kad , G. L. 1987 . J. Indian Chem. Soc. , 64 : 756
  • Buss , A. D. and Warren , S. 1983 . Tetrahedron Lett. , 24 : 111
  • Alternatively, compound 10 was obtained in 40% overall yield by reaction between a large molar excess of solid carbon dioxide and the 1-lithium 1-alkyne derived from 6, followed by treatment of the crude carboxylic acid so prepared with methanol in the presence of a catalytic amount of sulfuric acid.
  • On the basis of the literature data on the palladium-catalyzed cross-coupling reaction between stereodefined allylic acetates and organostannanes (Ref 10), we expected that this reaction afforded stereoisomerically pure (Z)-1
  • Suzuki , S. , Shiono , M. and Fujita , Y. 1983 . Synthesis , : 804
  • Fukamiya , N. , Oki , M. , Okano , M. and Aratani , T. 1981 . Chem. Ind. (London) , : 96 For syntheses of optically active 2, which are based on the use of (+)- or (-)- limonene as starting material, see:
  • Suga , K. , Kikuchi , H. , Watanabe , S. , Fujita , T. and Takiguchi , R. 1978 . Yukagaku , 27 : 802
  • 1979 . Chem. Abstr. , 90 : 168744c
  • Mehta , G. and Reddy , A. V. 1979 . Tetrahedron Lett. , : 2625
  • Crawford , R. J. , Erman , W. F. and Broaddus , C. D. 1972 . J. Am. Chem. Soc. , 94 : 4298
  • Wu , D. , Dan , Y. and Yan , B. 1985 . Huadong Huagong Xuenyuan Xuebao , 11 : 447 For syntheses of racemic 2, see:
  • 1987 . Chem. Abstr. , 107 : 115804k
  • Duan , Y. , Wu , D. , Chu , J. , Wang , M. and Yan , B. 1985 . Yiyao Gongye , 16 : 120
  • 1985 . Chem. Abstr. , 103 : 160708k
  • Sakurai , H. , Hosomi , A. , Saito , M. , Sasaki , K. , Iguchi , H. , Sasaki , J-I. and Araki , Y. 1983 . Tetrahedron , 39 : 883
  • Hosomi , A. , Iguchi , H. , Sasaki , J-I. and Sakurai , H. 1982 . Tetrahedron Lett. , 23 : 551
  • Ho , T-L. 1981 . Synth. Commun. , 11 : 237
  • Ho , T-L. and Liu , S-H. 1980 . Synth. Commun. , 10 : 603
  • Vig , O. P. , Sharma , S. D. , Matta , K. L. and Sehgal , J. M. 1971 . J. Indian Chem. Soc. , 48 : 993
  • Vig , O. P. , Vig , B. and Kapur , J. C. 1969 . J. Indian Chem. Soc. , 46 : 1078
  • Vig , O. P. , Salota , J. P. , Vig , B. and Ram , B. 1967 . Indian J. Chem. , 5 : 475
  • Manjarrez , A. and Guzman , A. 1966 . J. Org. Chem. , 31 : 348
  • Vig , O. P. , Matta , K. L. , Singh , G. and Raj , I. 1966 . J. Indian Chem. Soc. , 43 : 27
  • McCormick , J. P. and Barton , D. L. 1975 . J. Chem. Soc. Chem. Commun. , : 303
  • Tour , J. M. , Bedworth , P. V. and Wu , R. 1989 . Tetrahedron Lett. , 30 : 3927
  • Coulson , D. R. 1971 . Inorg. Synth. , 13 : 121
  • Ukai , T. , Kawazura , H. , Ishii , Y. , Bonnet , J. J. and Ibers , J. A. 1974 . J. Organomet. Chem. , 65 : 253
  • Takahashi , Y. , Ito , T. , Sakai , S. and Ishii , Y. 1970 . J. Chem. Soc. D , : 1065
  • Rettig , M. F. and Maitlis , P. 1971 . Inorg. Synth. , 17 : 134
  • Krapcho , A. P. and Jahngen , E. G. E. Jr . 1974 . J. Org. Chem. , 39 : 1322
  • Nazarov , I. N. and Azerbaev , I. N. 1948 . Zhur. Obschei Khim. , 18 : 414
  • Sheffy , F. K. , Godschalx , J. P. and Stille , J. K. 1984 . J. Am. Chem. Soc. , 106 : 4833
  • Nouguier , R. and Surzur , J-M. 1973 . Bull. Soc. Chim. Fr. , : 2399
  • Monti , S. A. and White , G. L. 1975 . J. Org. Chem. , 40 : 215
  • McCrae , D. A. and Dolby , L. 1977 . J. Org. Chem. , 42 : 1607
  • Büchi , G. and Powell , J. E. Jr. 1970 . J. Am. Chem. Soc. , 92 : 3126
  • Ipaktschi , J. 1986 . Z. Naturforsch. , 41b : 496
  • Davisson , V. J. and Poulter , C. D. 1993 . J. Am. Chem. Soc. , 115 : 1245
  • Gilbert , J. C. and Kelly , T. A. 1986 . J. Org. Chem. , 51 : 4485
  • Ismailov , A. G. , Agaev , A. N. , Atakishieva , M. R. and Salimova , B. A. 1966 . Izv. Vyssh. Uchebn. Zaved., Neft Gaz , 9 : 49
  • Julia , M. , Julia , S. and Guégan , R. 1960 . Bull. Soc. Chim. Fr. , : 1072
  • Biernacki , W. and Gdula , A. 1979 . Synthesis , : 37

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