A concise, stereoselective synthesis of (±)-geissoschizine

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9105-9106

  Bennasar, M Lluïsa ^a   Jiménez, Juan Miguel ^a   Sufi, Bilal A ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GEISSOSCHIZINE; INDOLE ALKALOID;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030577464     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02097-7     Document Type: Article

References (17)

1. 1. (a) Brown, R. T. In Indoles, The Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4. pp 63-146.
2. 1. (a) Brown, R. T. In Indoles, The Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4. pp 63-146.
3. (b) Szántay, C.; Blaskó, G.; Honty, K.; Dörnyei, G. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1986; Vol. 27, pp 131-268.
4. (c) Lounasmaa, M.; Tolvanen, A. In Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Vol. 25, Supplement to Part 4, pp 57-159.
5. (c) Lounasmaa, M.; Tolvanen, A. In Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Vol. 25, Supplement to Part 4, pp 57-159.
6. 2. For previous stereoselective syntheses of geissoschizine, see: (a) Martin, S. F.; Benage, B.; Hunter, J. E. J. Am. Chem. Soc. 1988, 110, 5925-5927.
7. (b) Overman, L. E.; Robichaud, A. J. J. Am. Chem. Soc. 1989, 111, 300-308.
8. 3. For a review, see: Bennasar, M.-L.; Bosch, J. Synlett 1995, 587-596.
9. 4. Bennasar, M.-L.; Jiménez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, in press.
10. 5. All new compounds gave satisfactory spectral, analytical and/or HRMS data. All yields are from material purified by column chromatography.
11. 6. For a review, see: Bosch, J.; Bennasar, M.-L. Heterocycles 1983, 20, 2471-2511.
12. 7. The closure of C ring of indolo[2,3-α]quinolizidines by Pummerer reaction has only been reported very recently: Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. Tetrahedron Lett. 1996, 37, 3071-3074.
13. 13C-NMR (75 MHz) 12.5 (C-18), 25.9 (C-15), 30.5 (C-14), 39.8 (C-6), 45.4 (C-16), 51.9 (C-21), 53.6 (C-3), 58.0 (C-5), 114.2 (C-12), 117.9 (C-7), 120.0 (C-9), 120.9 (C-19), 123.3 (C-10), 124.9 (C-11), 128.5 (C-8), 136.2 (C-2, C-20), 137.4 (C-13), 174.1 (C-22).
14. 2O, the tetracyclic sulfide 9 was isolated in 50% yield. For precedents of this abnormal Pummerer reaction, see: (a) Pyne, S. G.; Hajipour, A. R. Tetrahedron 1994, 50, 13501-13510.
15. (b) Arnone, A.; Bravo, P.; Bruché, L.; Cruacianelli, M.; Vichi, L.; Zanda, M. Tetrahedron Lett. 1995, 36, 7301-7304.
16. (c) Amat, M.; Bennasar, M.-L.; Hadida, S.; Sufi, B. A.: Zulaica, E.: Bosch, J. Tetrahedron Lett. 1996, 29, 5217-5220.
17. 10. Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908-909.