Enantio- and diastereocontrolled synthesis of (-)-19(S)-acetoxy-N1- acetyl-20-epitubifolidine

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3765-3768

  Shin, Kogyoku ^a   Moriya, Minoru ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Cyclization; Enantiocontrol; Indolization; Natural products

Indexed keywords

19 ACETOXY N1 ACETYL 20 EPITUBIFOLIDINE; ALKALOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY;

STRYCHNOS;

EID: 0032575166     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00597-8     Document Type: Article

References (25)

1. [1] Takano, S.; Satoh, S.; Ogasawara, K. J. Chem. Soc., Chem. Commun., 1988, 59-60.
2. [2] Takano, S.; Satoh, S.; Ogasawara, K.; Aoe, K. Heterocycles, 1990, 30, 583-605.
3. [3] Tietze , L. F.; Beifuss, U. Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, Oxford, 1991, Vol. 2, pp. 341-394.
4. [4] A pertinent review, see: Bosch, J.; Bonjoch, J.; Amat, M. The Alkaloids, ed. G. A. Cordell, Academic Press, San Diego, 1996, Vol. 48, pp. 75-189.
5. [5] Saxton, J. E.; Nat. Prod. Rep., 1997, 14, 559 and the former reports.
6. [6] Corey, E. J.; Fuchs, P. L. Tetrahedron Lett., 1972, 3769-3772.
7. [7] Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett., 1975, 4467-4470.
8. [8] Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles, 1986, 24, 31-32.
9. [9] Utilization of this procedure for the natural product synthesis: Takano, S.; Sato, T.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun., 1991, 462-464. Shin, K.; Ogasawara, K. Chem. Lett., 1995, 289-290. Shin, K.; Ogasawara, K. Synlett, 1995, 859-860. Shin, K.; Ogasawara, K. Synlett, 1996, 922-924. Saito, M.; Kawamura, M.; Hiroya, K.; Ogasawara, K. Chem. Commun., 1997, 765-766.
10. [9] Utilization of this procedure for the natural product synthesis: Takano, S.; Sato, T.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun., 1991, 462-464. Shin, K.; Ogasawara, K. Chem. Lett., 1995, 289-290. Shin, K.; Ogasawara, K. Synlett, 1995, 859-860. Shin, K.; Ogasawara, K. Synlett, 1996, 922-924. Saito, M.; Kawamura, M.; Hiroya, K.; Ogasawara, K. Chem. Commun., 1997, 765-766.
11. [9] Utilization of this procedure for the natural product synthesis: Takano, S.; Sato, T.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun., 1991, 462-464. Shin, K.; Ogasawara, K. Chem. Lett., 1995, 289-290. Shin, K.; Ogasawara, K. Synlett, 1995, 859-860. Shin, K.; Ogasawara, K. Synlett, 1996, 922-924. Saito, M.; Kawamura, M.; Hiroya, K.; Ogasawara, K. Chem. Commun., 1997, 765-766.
12. [9] Utilization of this procedure for the natural product synthesis: Takano, S.; Sato, T.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun., 1991, 462-464. Shin, K.; Ogasawara, K. Chem. Lett., 1995, 289-290. Shin, K.; Ogasawara, K. Synlett, 1995, 859-860. Shin, K.; Ogasawara, K. Synlett, 1996, 922-924. Saito, M.; Kawamura, M.; Hiroya, K.; Ogasawara, K. Chem. Commun., 1997, 765-766.
13. [9] Utilization of this procedure for the natural product synthesis: Takano, S.; Sato, T.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun., 1991, 462-464. Shin, K.; Ogasawara, K. Chem. Lett., 1995, 289-290. Shin, K.; Ogasawara, K. Synlett, 1995, 859-860. Shin, K.; Ogasawara, K. Synlett, 1996, 922-924. Saito, M.; Kawamura, M.; Hiroya, K.; Ogasawara, K. Chem. Commun., 1997, 765-766.
14. [10] Mitsunobu, O. Synthesis, 1981, 1-28. Hughes, D. L. Organic Reactions, 1992, 42, 335-656. Hughes, D. L. Org. Prep. Proced. Int., 1996, 28, 127-164.
15. [10] Mitsunobu, O. Synthesis, 1981, 1-28. Hughes, D. L. Organic Reactions, 1992, 42, 335-656. Hughes, D. L. Org. Prep. Proced. Int., 1996, 28, 127-164.
16. [10] Mitsunobu, O. Synthesis, 1981, 1-28. Hughes, D. L. Organic Reactions, 1992, 42, 335-656. Hughes, D. L. Org. Prep. Proced. Int., 1996, 28, 127-164.
17. [11] Bosch, J.; Amat, M. Tetrahedron Lett., 1985, 26, 4951-4954. Amat, M.; Linares, A.; Salas, M. -L.; Alvarez, M.; Bosch, J. J. Chem. Soc. Chem. Commun., 1988, 420-421. Amat, M.; Linares, A.; Bosch, J. J. Org. Chem., 1990, 55, 6299-6312. Gracia, J.; Bonjoch, J.; Casamitjana, N.; Amat , M.; Bosch, J. J. Chem. Soc., Chem. Commun., 1991, 614-615. Gracia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem., 1994, 59, 3939-3951.
18. [11] Bosch, J.; Amat, M. Tetrahedron Lett., 1985, 26, 4951-4954. Amat, M.; Linares, A.; Salas, M. -L.; Alvarez, M.; Bosch, J. J. Chem. Soc. Chem. Commun., 1988, 420-421. Amat, M.; Linares, A.; Bosch, J. J. Org. Chem., 1990, 55, 6299-6312. Gracia, J.; Bonjoch, J.; Casamitjana, N.; Amat , M.; Bosch, J. J. Chem. Soc., Chem. Commun., 1991, 614-615. Gracia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem., 1994, 59, 3939-3951.
19. [11] Bosch, J.; Amat, M. Tetrahedron Lett., 1985, 26, 4951-4954. Amat, M.; Linares, A.; Salas, M. -L.; Alvarez, M.; Bosch, J. J. Chem. Soc. Chem. Commun., 1988, 420-421. Amat, M.; Linares, A.; Bosch, J. J. Org. Chem., 1990, 55, 6299-6312. Gracia, J.; Bonjoch, J.; Casamitjana, N.; Amat , M.; Bosch, J. J. Chem. Soc., Chem. Commun., 1991, 614-615. Gracia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem., 1994, 59, 3939-3951.
20. [11] Bosch, J.; Amat, M. Tetrahedron Lett., 1985, 26, 4951-4954. Amat, M.; Linares, A.; Salas, M. -L.; Alvarez, M.; Bosch, J. J. Chem. Soc. Chem. Commun., 1988, 420-421. Amat, M.; Linares, A.; Bosch, J. J. Org. Chem., 1990, 55, 6299-6312. Gracia, J.; Bonjoch, J.; Casamitjana, N.; Amat , M.; Bosch, J. J. Chem. Soc., Chem. Commun., 1991, 614-615. Gracia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem., 1994, 59, 3939-3951.
21. [11] Bosch, J.; Amat, M. Tetrahedron Lett., 1985, 26, 4951-4954. Amat, M.; Linares, A.; Salas, M. -L.; Alvarez, M.; Bosch, J. J. Chem. Soc. Chem. Commun., 1988, 420-421. Amat, M.; Linares, A.; Bosch, J. J. Org. Chem., 1990, 55, 6299-6312. Gracia, J.; Bonjoch, J.; Casamitjana, N.; Amat , M.; Bosch, J. J. Chem. Soc., Chem. Commun., 1991, 614-615. Gracia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem., 1994, 59, 3939-3951.
22. [12] (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C. -K. J. Am. Chem. Soc., 1986, 108, 2468-2469.
23. (b) Nicolaou, K. C.; Prasad, C. V. C.; Hwang, C. -K.; Duggan, M. E.; Veale, C. A. J. Am. Chem. Soc., 1989, 111, 5321-5330.
24. [13] Schumann, D.; Schmid, H. Helv. Chim. Acta, 1963, 46, 1996-2003.
25. 3: 368.2100. Found: 368.2084.