View PDF Version
 
DOI: 10.1039/A604266J (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 113-120

Tandem Beckmann and Huisgen–White rearrangement of the 9-azabicyclo[3.3.1]nonan-3-one system. Part 2.1 The second mode of the rearrangement leading to 6-(prop-1-enyl)piperidin-2-ylacetic acid, a versatile intermediate for the syntheses of piperidine alkaloids (+)-pinidine and (+)-monomorine I

(Note: The full text of this document is currently only available in the PDF Version )

Osamu Muraoka, Bao-Zhong Zheng, Kazuhito Okumura, Emi Tabata, Genzoh Tanabe and Michinori Kubo

Abstract

The second mode of the Huisgen–White rearrangement of the bicyclic lactam, (-)-2-ethyl-4-oxo-3,10-diazabicyclo[4.3.1]decane (-)-13, leading to cis-[6-(prop-1-enyl)piperidin-2-yl]acetic acid (-)-9a under alkaline conditions is described. A reasonable reaction mechanism accounting for the preferable formation of the (E)-propenyl isomer (E)-9a is presented. Conversions of the olefinic acid 9a into two piperidine alkaloids (+)-pinidine (+)-10 and (-)-dihydropinidine (-)-21, and (-)-cis-2-formyl-6-methylpiperidine (-)-22, a key synthetic intermediate for an ants’ trail pheromone (+)-monomorine I (+)-11, are also described.

References

  1. Part 1, O. Muraoka, B.-Z. Zheng, K. Okumura, G. Tanabe, T. Momose and C. H. Eugster, J. Chem. Soc., Perkin Trans. 1, 1996, 1567 Search PubMed.
  2. G. R. Krow, Tetrahedron, 1981, 37, 2697 CrossRef CAS.
  3. T. Momose, O. Muraoka, S. Atarashi and T. Horita, Chem. Pharm. Bull., 1979, 27, 222 CAS; T. Momose, S. Atarashi and O. Muraoka, Tetrahedron Lett., 1974, 3697 CrossRef CAS.
  4. (a) W. H. Tallent, V. L. Stromberg and E. C. Horning, J. Am. Chem. Soc., 1955, 77, 6361 CrossRef CAS; (b) W. H. Tallent and E. C. Horning, J. Am. Chem. Soc., 1956, 78, 4467 CrossRef CAS; (c) J. N. Tawara, F. R. Stermitz and A. V. Blokhin, Phytochemistry, 1995, 39, 705 CrossRef CAS; (d) E. Leete and R. A. Carver, J. Org. Chem., 1975, 40, 2151 CrossRef CAS; (e) R. E. Dolle, K. I. Osifo and C.-H. Li, Tetrahedron Lett., 1991, 32, 5029 CrossRef CAS; (f) H. Takahata, H. Bandoh, M. Hanayama and T. Momose, Tetrahedron: Asymmetry, 1992, 3, 607 CrossRef CAS; (g) W. Oppolzer and E. Merifield, Helv. Chim. Acta, 1993, 76, 957 CrossRef CAS and references cited therein.
  5. (a) F. J. Ritter, I. E. M. Rotgans, E. Talman, P. E. J. Verwiel and F. Stein, Experientia, 1973, 29, 530 Search PubMed; (b) F. J. Ritter and C. J. Persoons, Neth. J. Zool., 1975, 25, 261 (Chem. Abstr., 1976, 84, 148018s) Search PubMed; (c) T. Nagasaki, H. Kato, H. Hayashi, M. Shioda, H. Hikasa and F. Hamaguchi, Heterocycles, 1990, 30, 561; (d) T. Momose, N. Toyooka, S. Seki and Y. Hirai, Chem. Pharm. Bull., 1990, 38, 2072 CAS; (e) M. Ito and C. Kibayashi, Tetrahedron Lett., 1990, 31, 5065 CrossRef CAS; (f) C. Saliou, A. Fleurant, J. P. Célérier and G. Lhommet, Tetrahedron Lett., 1991, 32, 3365 CrossRef CAS; (g) M. Ito and C. Kibayashi, Tetrahedron, 1991, 47, 9329 CrossRef CAS; (h) M. Vavrecka and M. Hesse, Helv. Chim. Acta, 1991, 74, 438 CrossRef CAS; (i) C. W. Jefford, Q. Tang and A. Zaslona, J. Am. Chem. Soc., 1991, 113, 3513 CrossRef CAS; (j) E. Zeller and D. S. Grierson, Synlett, 1991, 878 CrossRef CAS; (k) P. L. MacGrane and T. Livinghouse, J. Org. Chem., 1992, 57, 1323 CrossRef CAS; (l) S. R. Angle and J. G. Breitenbucher, Tetrahedron Lett., 1993, 34, 3985 CrossRef CAS; (m) H. Takahata, H. Bandoh and T. Momose, Tetrahedron, 1993, 49, 11205 CrossRef; (n) K. Higashiyama, K. Nakahata and H. Takahashi, J. Chem. Soc., Perkin Trans. 1, 1994, 351 RSC; (o) D. R. Artis, I.-S. Cho, S. Jaime-Figueroa and J. M. Muchowski, J. Org. Chem., 1994, 59, 2456 CrossRef CAS; (p) M. J. Munchhof and A. I. Meyers, J. Am. Chem. Soc., 1995, 117, 5399 CrossRef CAS and references cited therein.
  6. E. H. White and D. J. Woodcock, in The Chemistry of the Amino Group, ed. S. Patai, Interscience Publishers, London, 1968, p. 440 Search PubMed.
  7. E. J. Corey and E. A. Broger, Tetrahedron Lett., 1969, 1779 CrossRef CAS; A. Ito, R. Takahashi and Y. Baba, Chem. Pharm. Bull., 1975, 23, 3081 CAS.
  8. (a) A. B. Attygalle, S.-C. Xu, K. D. McCormick, J. Meinwald, C. L. Blankespoor and T. Eisner, Tetrahedron, 1993, 49, 9333 CrossRef CAS; (b) T. Momose, N. Toyooka and Y. Hirai, Chem. Lett., 1990, 1319 CAS; (c) D. L. Comins and M. A. Weglarz, J. Org. Chem., 1991, 56, 2506 CrossRef CAS; (d) E. Theodorakis, J. Royer and H.-P. Husson, Synth. Commun., 1991, 21, 521 CAS; (e) K. Higashiyama, K. Nakahata and H. Takahashi, Heterocycles, 1992, 33, 17 CAS; (f) Z.-H. Lu and W.-S. Zhou, J. Chem. Soc., Perkin Trans. 1, 1993, 593 RSC; (g) D. L. Comins, G. Chung and M. A. Foley, Heterocycles, 1994, 37, 1121 CrossRef CAS; (h) T.-K. Yang, T.-F. Teng, J.-H. Lin and Y.-Y. Lay, Tetrahedron Lett., 1994, 35, 3581 CrossRef CAS and references cited therein.
  9. B. Nader, T. R. Bailey, R. W. Franck and S. M. Weinreb, J. Am. Chem. Soc., 1981, 103, 7573 CrossRef CAS.
  10. C. J. Gilmore, J. Appl. Crystallogr., 1984, 17, 42 CrossRef CAS.
  11. TEXSAN: TEXRAY Structure Analysis Package, Molecular Structures Corporation, The Woodland, Texas, 1985.