Stereocontrolled elongation of a functionalized isoprene unit on the E or Z terminal methyl of terpenoids via N-ylide rearrangement of the common ammonium salts

Chemistry Letters

Volumn , Issue 5, 1996, Pages 385-386

  Honda, Kiyoshi ^a   Tabuchi, Masayuki ^a   Inoue, Seiichi ^a  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030501645     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.385     Document Type: Article

References (19)

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2. D. J. Faulkner, Synthesis, 1971, 175; S. Inoue and K. Honda, J. Syn. Org. Chem., Jpn., 51, 894 (1993). For reviews of [2,3]rearrangement, see: R. W. Hoffmann, Angew. Chem. Int. Ed. Engl., 18, 563 (1979); T. Nakai and K. Mikami, Chem. Rev., 86, 885 (1986); K. Mikami and T. Nakai, Synthesis , 1991, 594; T. Nakai and K. Mikami, Org. React., 46, 105 (1995). For reviews of [3,3]rearrangement, see: F. E. Ziegler, Chem. Rev., 88, 1423 (1988); G. B. Bennett, Synthesis, 1977, 589.
3. D. J. Faulkner, Synthesis, 1971, 175; S. Inoue and K. Honda, J. Syn. Org. Chem., Jpn., 51, 894 (1993). For reviews of [2,3]rearrangement, see: R. W. Hoffmann, Angew. Chem. Int. Ed. Engl., 18, 563 (1979); T. Nakai and K. Mikami, Chem. Rev., 86, 885 (1986); K. Mikami and T. Nakai, Synthesis , 1991, 594; T. Nakai and K. Mikami, Org. React., 46, 105 (1995). For reviews of [3,3]rearrangement, see: F. E. Ziegler, Chem. Rev., 88, 1423 (1988); G. B. Bennett, Synthesis, 1977, 589.
4. D. J. Faulkner, Synthesis, 1971, 175; S. Inoue and K. Honda, J. Syn. Org. Chem., Jpn., 51, 894 (1993). For reviews of [2,3]rearrangement, see: R. W. Hoffmann, Angew. Chem. Int. Ed. Engl., 18, 563 (1979); T. Nakai and K. Mikami, Chem. Rev., 86, 885 (1986); K. Mikami and T. Nakai, Synthesis , 1991, 594; T. Nakai and K. Mikami, Org. React., 46, 105 (1995). For reviews of [3,3]rearrangement, see: F. E. Ziegler, Chem. Rev., 88, 1423 (1988); G. B. Bennett, Synthesis, 1977, 589.
5. D. J. Faulkner, Synthesis, 1971, 175; S. Inoue and K. Honda, J. Syn. Org. Chem., Jpn., 51, 894 (1993). For reviews of [2,3]rearrangement, see: R. W. Hoffmann, Angew. Chem. Int. Ed. Engl., 18, 563 (1979); T. Nakai and K. Mikami, Chem. Rev., 86, 885 (1986); K. Mikami and T. Nakai, Synthesis , 1991, 594; T. Nakai and K. Mikami, Org. React., 46, 105 (1995). For reviews of [3,3]rearrangement, see: F. E. Ziegler, Chem. Rev., 88, 1423 (1988); G. B. Bennett, Synthesis, 1977, 589.
6. D. J. Faulkner, Synthesis, 1971, 175; S. Inoue and K. Honda, J. Syn. Org. Chem., Jpn., 51, 894 (1993). For reviews of [2,3]rearrangement, see: R. W. Hoffmann, Angew. Chem. Int. Ed. Engl., 18, 563 (1979); T. Nakai and K. Mikami, Chem. Rev., 86, 885 (1986); K. Mikami and T. Nakai, Synthesis , 1991, 594; T. Nakai and K. Mikami, Org. React., 46, 105 (1995). For reviews of [3,3]rearrangement, see: F. E. Ziegler, Chem. Rev., 88, 1423 (1988); G. B. Bennett, Synthesis, 1977, 589.
7. D. J. Faulkner, Synthesis, 1971, 175; S. Inoue and K. Honda, J. Syn. Org. Chem., Jpn., 51, 894 (1993). For reviews of [2,3]rearrangement, see: R. W. Hoffmann, Angew. Chem. Int. Ed. Engl., 18, 563 (1979); T. Nakai and K. Mikami, Chem. Rev., 86, 885 (1986); K. Mikami and T. Nakai, Synthesis , 1991, 594; T. Nakai and K. Mikami, Org. React., 46, 105 (1995). For reviews of [3,3]rearrangement, see: F. E. Ziegler, Chem. Rev., 88, 1423 (1988); G. B. Bennett, Synthesis, 1977, 589.
8. D. J. Faulkner, Synthesis, 1971, 175; S. Inoue and K. Honda, J. Syn. Org. Chem., Jpn., 51, 894 (1993). For reviews of [2,3]rearrangement, see: R. W. Hoffmann, Angew. Chem. Int. Ed. Engl., 18, 563 (1979); T. Nakai and K. Mikami, Chem. Rev., 86, 885 (1986); K. Mikami and T. Nakai, Synthesis , 1991, 594; T. Nakai and K. Mikami, Org. React., 46, 105 (1995). For reviews of [3,3]rearrangement, see: F. E. Ziegler, Chem. Rev., 88, 1423 (1988); G. B. Bennett, Synthesis, 1977, 589.
9. S. H. Pine, Org. React., 18, 403 (1970); A. R. Lepley and A. Giumanini, In "Mechanisms of Molecular Migrations," ed by B. S. Thyagarajan, Interscience, New York (1971), Vol. 3, p297; T. S. Stevens and W. E. Watts, "Selected Molecular Rearrangements," van Nostrand-Reinhold, London (1973), p81.
10. S. H. Pine, Org. React., 18, 403 (1970); A. R. Lepley and A. Giumanini, In "Mechanisms of Molecular Migrations," ed by B. S. Thyagarajan, Interscience, New York (1971), Vol. 3, p297; T. S. Stevens and W. E. Watts, "Selected Molecular Rearrangements," van Nostrand-Reinhold, London (1973), p81.
11. S. H. Pine, Org. React., 18, 403 (1970); A. R. Lepley and A. Giumanini, In "Mechanisms of Molecular Migrations," ed by B. S. Thyagarajan, Interscience, New York (1971), Vol. 3, p297; T. S. Stevens and W. E. Watts, "Selected Molecular Rearrangements," van Nostrand-Reinhold, London (1973), p81.
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14. K. Honda and S. Inoue, Synlett, 1994, 739.
15. S. G. Hegde, M. K. Vogel, J. Saddler, T. Hrinyo, N. Rockwell, R. Haynes, M. Oliver, and J. Wolinsky, Tetrahedron Lett., 21, 441 (1980).
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17. A. Loeffler, R. J. Pratt, H. P. Ruesch, and A. S. Dreiding, Helv. Chim. Acta, 53, 383 (1970). A 2 : 1 mixture of γ-bromotiglate and β′-bromo isomer was used for the reaction. The latter was recovered unchanged after the reaction by extraction with ether.
18. 3) δ 1.61(s, 3H), 1.67(s, 3H), 2.0-2.7(m, 8H), 3.99(s 2H), 5.01(m, 2H), 5.06(d, J = 10.9 Hz, 1H), 5.1-5.3(m, 1H), 5.24(d, J = 17.8 Hz, 1H), 5.40(t, J = 8 Hz, 1H), and 6.38(dd, J = 10.9, 17.8 Hz, 1H).
19. M. J. Jorgenson, Tetrahedron Lett., 1962, 559.