2-Piperidone type of chiral building block for 3-piperidinol alkaloid synthesis

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4914-4919

  Toyooka, Naoki ^a   Yoshida, Yasuko ^a   Yotsui, Yasuhito ^a   Momose, Takefumi ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PIPERIDONE; 3 PIPERIDINOL ALKALOID; ISO 6 CASSINE; LACTAM DERIVATIVE; PIPERIDINE DERIVATIVE; PROSAFRININE; PROSOPHYLLINE; PROSOPININE; SPECTALINE; UNCLASSIFIED DRUG; URETHAN DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; ESTERIFICATION; REACTION ANALYSIS; SCHIZOSACCHAROMYCES POMBE; STEREOCHEMISTRY;

EID: 0033603564     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990397t     Document Type: Article

References (59)

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2. For reviews, see: Wang, C.-L. J.; Wuorola, M. A. Org. Prep. Proced. Int. 1992, 24, 585-621. Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 44, pp 189-256. Michael, J. P. Nat. Prod. Rep. 1995, 12, 535-552. Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493-3513. Daly, J. W. In The Alkaloids, Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 50, pp 141-169.
3. For reviews, see: Wang, C.-L. J.; Wuorola, M. A. Org. Prep. Proced. Int. 1992, 24, 585-621. Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 44, pp 189-256. Michael, J. P. Nat. Prod. Rep. 1995, 12, 535-552. Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493-3513. Daly, J. W. In The Alkaloids, Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 50, pp 141-169.
4. For reviews, see: Wang, C.-L. J.; Wuorola, M. A. Org. Prep. Proced. Int. 1992, 24, 585-621. Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 44, pp 189-256. Michael, J. P. Nat. Prod. Rep. 1995, 12, 535-552. Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493-3513. Daly, J. W. In The Alkaloids, Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 50, pp 141-169.
5. For reviews, see: Wang, C.-L. J.; Wuorola, M. A. Org. Prep. Proced. Int. 1992, 24, 585-621. Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 44, pp 189-256. Michael, J. P. Nat. Prod. Rep. 1995, 12, 535-552. Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493-3513. Daly, J. W. In The Alkaloids, Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 50, pp 141-169.
6. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929- 5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095- 2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
7. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929- 5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095- 2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
8. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929-5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095- 2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
9. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929- 5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095- 2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
10. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929- 5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095- 2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
11. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929- 5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095- 2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
12. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929- 5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095- 2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
13. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929- 5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095- 2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
14. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929- 5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095- 2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
15. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929- 5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
16. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, pp 89-183. Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309-2313. Bolzani, V. da S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929- 5934. Astudillo, S. L.; Jürgens, S. K.; SchmedaHirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med. 1999, 65, 161-162 and references therein. For recent synthesis of this type of alkaloids, see: Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095- 2096. Kiguchi, T.; Shirakawa, M.; Honda, R.; Ninomiya, I.; Naito, T. Tetrahedron 1998, 54, 15589-15606 and references therein.
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22. It was worthwhile noting Comins' work in the field of enantioselective synthesis of various alkaloids using chiral nonracemic 2,3-dihydro-4-pyridones (5,6-didehydro-4-piperidones); see: Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J.; Concolino, T. E.; Rheingold, A. L. J. Am. Chern. Soc. 1999, 121, 2651-2652. Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509-2510. Comins, D. L.; Chen, X.; Morgan, L. A. J. Org. Chem. 1997, 62, 7435- 7438. Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182-8187. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycle; JAI Press Inc., 1996; Vol. 2, pp 251-294 and references therein.
23. It was worthwhile noting Comins' work in the field of enantioselective synthesis of various alkaloids using chiral nonracemic 2,3- dihydro-4-pyridones (5,6-didehydro-4-piperidones); see: Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J.; Concolino, T. E.; Rheingold, A. L. J. Am. Chern. Soc. 1999, 121, 2651-2652. Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509-2510. Comins, D. L.; Chen, X.; Morgan, L. A. J. Org. Chem. 1997, 62, 7435- 7438. Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182-8187. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycle; JAI Press Inc., 1996; Vol. 2, pp 251-294 and references therein.
24. It was worthwhile noting Comins' work in the field of enantioselective synthesis of various alkaloids using chiral nonracemic 2,3- dihydro-4-pyridones (5,6-didehydro-4-piperidones); see: Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J.; Concolino, T. E.; Rheingold, A. L. J. Am. Chern. Soc. 1999, 121, 2651-2652. Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509-2510. Comins, D. L.; Chen, X.; Morgan, L. A. J. Org. Chem. 1997, 62, 7435-7438. Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182-8187. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycle; JAI Press Inc., 1996; Vol. 2, pp 251-294 and references therein.
25. It was worthwhile noting Comins' work in the field of enantioselective synthesis of various alkaloids using chiral nonracemic 2,3- dihydro-4-pyridones (5,6-didehydro-4-piperidones); see: Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J.; Concolino, T. E.; Rheingold, A. L. J. Am. Chern. Soc. 1999, 121, 2651-2652. Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509-2510. Comins, D. L.; Chen, X.; Morgan, L. A. J. Org. Chem. 1997, 62, 7435- 7438. Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182-8187. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycle; JAI Press Inc., 1996; Vol. 2, pp 251-294 and references therein.
26. It was worthwhile noting Comins' work in the field of enantioselective synthesis of various alkaloids using chiral nonracemic 2,3- dihydro-4-pyridones (5,6-didehydro-4-piperidones); see: Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J.; Concolino, T. E.; Rheingold, A. L. J. Am. Chern. Soc. 1999, 121, 2651-2652. Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509-2510. Comins, D. L.; Chen, X.; Morgan, L. A. J. Org. Chem. 1997, 62, 7435- 7438. Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182-8187. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycle; JAI Press Inc., 1996; Vol. 2, pp 251-294 and references therein.
27. For preliminary accounts, see: Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718.
28. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672; J. Org. Chem. 1994, 59, 3575-3584.
29. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672; J. Org. Chem. 1994, 59, 3575-3584.
30. Isolation: (a) Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull Soc. Chim. Belg. 1972, 81, 443-458. Nonchiral synthesis: (b) Paterne, M.; Dhal, R.; Brown, E. Bull. Chem. Soc. Jpn. 1989, 62, 1321- 1324.
31. Isolation: (a) Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull Soc. Chim. Belg. 1972, 81, 443-458. Nonchiral synthesis: (b) Paterne, M.; Dhal, R.; Brown, E. Bull. Chem. Soc. Jpn. 1989, 62, 1321-1324.
32. Isolation: Christofidis, I.; Welter, A.; Jadot, J. Tetrahedron 1977, 33, 977-979.
33. Isolation: ref 7a. Nonchiral stereoselective synthesis: (a) Natume, M.; Ogawa, M. Heterocydes 1981, 16, 973. Chiral syntheses of desoxoprosophylline: (b) Saitoh, Y.; Moriyama, Y.; Takahashi, T.; Khuong-Huu, Q. Tetrahedron Lett. 1980, 75. (c) Saitoh, Y.; Moriyama, Y.; Hirota, H.; Takahashi, T.; Khuong-Huu, Q. Bull. Chem. Soc. Jpn. 1981, 54, 488. (d) Tadano, K.; Takao, K.; Nigawara, Y.; Nishio, E.; Takagi, I.; Maeda, K.; Ogawa, S. Synlett 1993, 565-567; (e) Tetrahedron 1994, 50, 5681-5704. (f) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. (g) Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. (h) Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999-8003.
34. Isolation: ref 7a. Nonchiral stereoselective synthesis: (a) Natume, M.; Ogawa, M. Heterocydes 1981, 16, 973. Chiral syntheses of desoxoprosophylline: (b) Saitoh, Y.; Moriyama, Y.; Takahashi, T.; Khuong-Huu, Q. Tetrahedron Lett. 1980, 75. (c) Saitoh, Y.; Moriyama, Y.; Hirota, H.; Takahashi, T.; Khuong-Huu, Q. Bull. Chem. Soc. Jpn. 1981, 54, 488. (d) Tadano, K.; Takao, K.; Nigawara, Y.; Nishio, E.; Takagi, I.; Maeda, K.; Ogawa, S. Synlett 1993, 565-567; (e) Tetrahedron 1994, 50, 5681-5704. (f) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. (g) Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. (h) Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999-8003.
35. Isolation: ref 7a. Nonchiral stereoselective synthesis: (a) Natume, M.; Ogawa, M. Heterocydes 1981, 16, 973. Chiral syntheses of desoxoprosophylline: (b) Saitoh, Y.; Moriyama, Y.; Takahashi, T.; Khuong-Huu, Q. Tetrahedron Lett. 1980, 75. (c) Saitoh, Y.; Moriyama, Y.; Hirota, H.; Takahashi, T.; Khuong-Huu, Q. Bull. Chem. Soc. Jpn. 1981, 54, 488. (d) Tadano, K.; Takao, K.; Nigawara, Y.; Nishio, E.; Takagi, I.; Maeda, K.; Ogawa, S. Synlett 1993, 565-567; (e) Tetrahedron 1994, 50, 5681-5704. (f) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. (g) Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. (h) Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999-8003.
36. Isolation: ref 7a. Nonchiral stereoselective synthesis: (a) Natume, M.; Ogawa, M. Heterocydes 1981, 16, 973. Chiral syntheses of desoxoprosophylline: (b) Saitoh, Y.; Moriyama, Y.; Takahashi, T.; Khuong-Huu, Q. Tetrahedron Lett. 1980, 75. (c) Saitoh, Y.; Moriyama, Y.; Hirota, H.; Takahashi, T.; Khuong-Huu, Q. Bull. Chem. Soc. Jpn. 1981, 54, 488. (d) Tadano, K.; Takao, K.; Nigawara, Y.; Nishio, E.; Takagi, I.; Maeda, K.; Ogawa, S. Synlett 1993, 565-567; (e) Tetrahedron 1994, 50, 5681-5704. (f) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. (g) Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. (h) Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999-8003.
37. Isolation: ref 7a. Nonchiral stereoselective synthesis: (a) Natume, M.; Ogawa, M. Heterocydes 1981, 16, 973. Chiral syntheses of desoxoprosophylline: (b) Saitoh, Y.; Moriyama, Y.; Takahashi, T.; Khuong-Huu, Q. Tetrahedron Lett. 1980, 75. (c) Saitoh, Y.; Moriyama, Y.; Hirota, H.; Takahashi, T.; Khuong-Huu, Q. Bull. Chem. Soc. Jpn. 1981, 54, 488. (d) Tadano, K.; Takao, K.; Nigawara, Y.; Nishio, E.; Takagi, I.; Maeda, K.; Ogawa, S. Synlett 1993, 565-567; (e) Tetrahedron 1994, 50, 5681-5704. (f) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. (g) Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. (h) Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999-8003.
38. Isolation: ref 7a. Nonchiral stereoselective synthesis: (a) Natume, M.; Ogawa, M. Heterocydes 1981, 16, 973. Chiral syntheses of desoxoprosophylline: (b) Saitoh, Y.; Moriyama, Y.; Takahashi, T.; Khuong-Huu, Q. Tetrahedron Lett. 1980, 75. (c) Saitoh, Y.; Moriyama, Y.; Hirota, H.; Takahashi, T.; Khuong-Huu, Q. Bull. Chem. Soc. Jpn. 1981, 54, 488. (d) Tadano, K.; Takao, K.; Nigawara, Y.; Nishio, E.; Takagi, I.; Maeda, K.; Ogawa, S. Synlett 1993, 565-567; (e) Tetrahedron 1994, 50, 5681-5704. (f) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. (g) Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. (h) Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999-8003.
39. Isolation: ref 7a. Nonchiral stereoselective synthesis: (a) Natume, M.; Ogawa, M. Heterocydes 1981, 16, 973. Chiral syntheses of desoxoprosophylline: (b) Saitoh, Y.; Moriyama, Y.; Takahashi, T.; Khuong-Huu, Q. Tetrahedron Lett. 1980, 75. (c) Saitoh, Y.; Moriyama, Y.; Hirota, H.; Takahashi, T.; Khuong-Huu, Q. Bull. Chem. Soc. Jpn. 1981, 54, 488. (d) Tadano, K.; Takao, K.; Nigawara, Y.; Nishio, E.; Takagi, I.; Maeda, K.; Ogawa, S. Synlett 1993, 565-567; (e) Tetrahedron 1994, 50, 5681-5704. (f) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. (g) Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. (h) Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999-8003.
40. Isolation: ref 7a. Nonchiral stereoselective synthesis: (a) Natume, M.; Ogawa, M. Heterocydes 1981, 16, 973. Chiral syntheses of desoxoprosophylline: (b) Saitoh, Y.; Moriyama, Y.; Takahashi, T.; Khuong-Huu, Q. Tetrahedron Lett. 1980, 75. (c) Saitoh, Y.; Moriyama, Y.; Hirota, H.; Takahashi, T.; Khuong-Huu, Q. Bull. Chem. Soc. Jpn. 1981, 54, 488. (d) Tadano, K.; Takao, K.; Nigawara, Y.; Nishio, E.; Takagi, I.; Maeda, K.; Ogawa, S. Synlett 1993, 565-567; (e) Tetrahedron 1994, 50, 5681-5704. (f) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887-3893. (g) Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228. (h) Ojima, I.; Vidal, E. S. J. Org. Chem. 1998, 63, 7999-8003.
41. Isolation: Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442. Chiral syntheses of prosopinine: Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777 and ref 9h. Chiral syntheses of desoxoprosopinine: Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473- 3475 and refs 8d and 8e. Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526; J. Chem. Soc., Perkin Trans. 1 1996, 793-802. Reference 9f. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Nonchiral stereoselective synthesis of desoxoprosopinine: Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
42. Isolation: Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442. Chiral syntheses of prosopinine: Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777 and ref 9h. Chiral syntheses of desoxoprosopinine: Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473- 3475 and refs 8d and 8e. Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526; J. Chem. Soc., Perkin Trans. 1 1996, 793-802. Reference 9f. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Nonchiral stereoselective synthesis of desoxoprosopinine: Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
43. Isolation: Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442. Chiral syntheses of prosopinine: Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777 and ref 9h. Chiral syntheses of desoxoprosopinine: Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475 and refs 8d and 8e. Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526; J. Chem. Soc., Perkin Trans. 1 1996, 793-802. Reference 9f. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Nonchiral stereoselective synthesis of desoxoprosopinine: Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
44. Isolation: Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442. Chiral syntheses of prosopinine: Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777 and ref 9h. Chiral syntheses of desoxoprosopinine: Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473- 3475 and refs 8d and 8e. Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526; J. Chem. Soc., Perkin Trans. 1 1996, 793-802. Reference 9f. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Nonchiral stereoselective synthesis of desoxoprosopinine: Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
45. Isolation: Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442. Chiral syntheses of prosopinine: Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777 and ref 9h. Chiral syntheses of desoxoprosopinine: Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473- 3475 and refs 8d and 8e. Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526; J. Chem. Soc., Perkin Trans. 1 1996, 793-802. Reference 9f. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Nonchiral stereoselective synthesis of desoxoprosopinine: Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
46. Isolation: Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442. Chiral syntheses of prosopinine: Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777 and ref 9h. Chiral syntheses of desoxoprosopinine: Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473- 3475 and refs 8d and 8e. Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526; J. Chem. Soc., Perkin Trans. 1 1996, 793-802. Reference 9f. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Nonchiral stereoselective synthesis of desoxoprosopinine: Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
47. Isolation: Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442. Chiral syntheses of prosopinine: Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777 and ref 9h. Chiral syntheses of desoxoprosopinine: Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473- 3475 and refs 8d and 8e. Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526; J. Chem. Soc., Perkin Trans. 1 1996, 793-802. Reference 9f. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Nonchiral stereoselective synthesis of desoxoprosopinine: Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
48. Isolation: Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442. Chiral syntheses of prosopinine: Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777 and ref 9h. Chiral syntheses of desoxoprosopinine: Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473- 3475 and refs 8d and 8e. Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526; J. Chem. Soc., Perkin Trans. 1 1996, 793-802. Reference 9f. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Nonchiral stereoselective synthesis of desoxoprosopinine: Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
49. Isolation: Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442. Chiral syntheses of prosopinine: Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777 and ref 9h. Chiral syntheses of desoxoprosopinine: Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473- 3475 and refs 8d and 8e. Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526; J. Chem. Soc., Perkin Trans. 1 1996, 793-802. Reference 9f. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Nonchiral stereoselective synthesis of desoxoprosopinine: Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
50. Isolation: Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-442. Chiral syntheses of prosopinine: Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777 and ref 9h. Chiral syntheses of desoxoprosopinine: Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473- 3475 and refs 8d and 8e. Yuasa, Y.; Ando, J.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 1525-1526; J. Chem. Soc., Perkin Trans. 1 1996, 793-802. Reference 9f. Agami, C.; County, F.; Mathieu, H. Tetrahedron Lett. 1998, 39, 3505-3508. Agami, C.; County, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796. Nonchiral stereoselective synthesis of desoxoprosopinine: Holmes, A. B.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1985, 37-39. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672. Luker, T.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3592-3596.
51. Bonjoch, J.; Serret, I.; Bosch, J. Tetrahedron 1984, 40, 2505-2511.
52. Seebach, D.; Roggo, S.; Maetzke, T.; Braunschweiger, H.; Cercus, J.; Krieger, M. Helv. Chim. Acta 1987, 70, 1605-1615.
53. 4 (6 equiv) at room temperature for 23 h gave a 1:1 mixture of (-)-4 and (-)-5. Reduction with DIBAL (2.2 equiv) at 0 °C for 1 h resulted in the formation of a complex mixture not including the desired alcohol (-)-5.
54. Johnson, F. Chem. Rev. 1968, 68, 375-413.
55. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp 209-290.
56. The enantiomeric excess was determined by HPLC analysis; see the Experimental Section in the Supporting Information.
57. Campbell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616.
58. Direct inversion of the hydroxyl in 48 under the Mitsunobu reaction conditions afforded the enamine derivative 46 (eq 1). (equation presented) This result was a contrast to the Mitsunobu inversion of the 2,3(trans)-to the 2,3(cis)-piperidinol derivative; see: Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664.
59. Jung, M. E.; Lyster, M. A. J. Am. Chem. Soc. 1977, 99, 968-969.