Stereoselective transformation of enantiopure cyclohexenol into cis-hydrindan. An enantioselective formal total synthetic route to (+)-pumiliotoxin C

Journal of Organic Chemistry

Volumn 61, Issue 24, 1996, Pages 8687-8691

  Toyota, Masahiro ^a   Asoh, Takanobu ^a   Matsuura, Masaki ^a   Fukumoto, Keiichiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDAN DERIVATIVE; PUMILIOTOXIN; PUMILIOTOXIN C; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029958031     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9613085     Document Type: Article

References (30)

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2. Physiological property: (a) Alkaloids: Chemical and Biological Perspectives, Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 4, p 162. (b) The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 43, p 185.
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8. Isolation: Daly, J. W.; Witkop, B.; Tokuyama, T.; Nishikawa, T.; Karle, I. L. Helv. Chim. Acta 1977, 60, 1128-1140.
9. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
10. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
11. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
12. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
13. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
14. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
15. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
16. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
17. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
18. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
19. For chiral syntheses of natural (-)-pumiliotoxin C: (a) Reference 4 (b) Bonin, M.; Royer, J.; Grielson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. (c) Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. (d) Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. (e) Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216. The unnatural (+)-epimer: (f) Reference 4. (g) Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. For recent syntheses of (±)-pumiliotoxin C: (h) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697-5700. (i) Braudi, A.; Cordero, F. M.; Goti, A.; Guarua, A. Tetrahedron Lett. 1992, 33, 6697-6700. (j) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. (k) Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660. (l) Mehta, G.; Praveen, M. J. Org. Chem. 1995, 60, 279-280.
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