Rearrangement of Aspidosperma alkaloids with a modified tryptamine chain. Revised structure of the Polonovski-Potier reaction product of 5-cyano-16-chloro-1-dehydrovincadifformine

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9614-9616

  Lewin, Guy ^a,b   Schaeffer, Corinne ^c   Morgant, Georges ^b   Nguyen Huy, Dung ^b  

^a Faculte de Pharmacie   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

^c INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

VINCA ALKALOID;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0030460966     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961373e     Document Type: Article

References (27)

1. For a general review on the chemistry of the Aspidosperma alkaloids, see: Saxton, J. E. Aapidospermine Group. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; John Wiley: New York, 1994; Suppl. to Vol. 25, Part IV, pp 377-391.
2. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
3. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
4. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
5. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
6. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
7. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
8. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
9. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
10. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
11. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
12. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
13. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
14. For a general review of the rearrangements of the Aspidosperma alkaloids, see: Cordell, G. A. In The Alkaloids; Manske, R. H. F., Rodrigo, R. G. A., Eds.; Academic Press: New York, 1979; Vol. 17, pp 267-296. For more recent studies on Aspidosperma alkaloid rearrangements, see: (a) Hugel, G.; Massiot, G.; Lévy, J.; Le Men, J. Tetrahedron 1981, 37, 1369-1375. (b) Lewin, G.; Poisson, J.; Lamotte Brasseur, J. Tetrahedron 1982, 38, 3291-3298. (c) Hugel, G.; Lévy, J. Tetrahedron 1983, 39, 1539-1542. (d) Hugel, G.; Lévy, J. Tetrahedron 1984, 40, 1067-1073. (e) Hugel, G.; Lévy, J. J. Org. Chem. 1984, 49, 3275-3277. (f) Palmisano, G.; Danieli, B.; Lesma, G.; Riva, R.; Riva, S.; Demartin, F.; Masciocchi, N. J. Org. Chem. 1984, 49, 4138-4143. (g) Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814. (h) Lewin, G.; Poisson, J.; Toffoli, P. Tetrahedron 1987, 43, 493-500. (i) Palmisano, G.; Danieli, B.; Lesma, G.; Trupiano, F.; Pilati, T. J. Org. Chem. 1988, 53, 1056-1064. (j) Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786. (k) Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636. (l) Lewin, G.; Schaeffer, C.; Lambert, P.-H. J. Org. Chem. 1995, 60, 3282-3287.
15. Lewin, G.; Poisson, J. Tetrahedron Lett. 1994, 35, 8153-8156.
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17. Numbering system proposed by Le Men, J.; Taylor, W. I. Experientia 1965, 21, 508-510.
18. For rearrangements of tabersonine or vincadifformine 16-chloroindolenines, see in ref 2 the general review (pp 283-284, 287-288) and refs 2b,c,g,j.
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21. Lewin, G.; Poisson, J. Tetrahedron Lett. 1984, 25, 3813-3814.
22. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
23. Lewin, G.; Poisson, J.; Schaeffer, C.; Volland, J. P. Tetrahedron 1990, 46, 7775-7786.
24. Hugel, G.; Royer, D.; Sigaut, F.; Lévy, J. J. Org. Chem. 1991, 56, 4631-4636.
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