Total synthesis of (-)-γ-lycorane using diastereoselective 5-endo-trig radical cyclization of N-vinylic α-halo amides

Synthesis

Volumn , Issue 12, 1998, Pages 1803-1806

  Ikeda, Masazumi ^a   Ohtani, Shinji ^a   Sato, Tatsunori ^a   Ishibashi, Hiroyuki ^b  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b KANAZAWA UNIVERSITY   (Japan)

Author keywords

( ) lycorane; 5 endo trig cyclization; Asymmetric induction; Radical cyclization; Tributylin hydride

Indexed keywords

ALPHA IODO N (6 OXOCYCLOHEX 1 ENYL) N (1 PHENYLETHYL)ACETAMIDE; AMIDE; GAMMA LYCORANE; INDOLE DERIVATIVE; NATURAL PRODUCT; OCTAHYDROINDOLE 2,7 DIONE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032416889     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2212     Document Type: Article

References (35)

1. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
2. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
3. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
4. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
5. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
6. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
7. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
8. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
9. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
10. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
11. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
12. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
13. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
14. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
15. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
16. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
17. Porter, N. A.; Lacher, B.; Chang, V. H.-T.; Magnin, D. R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J. G.; Curran, D. P.; Geib, S. J.; Rebek, J. Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D. P.; Shen, W.; Zhang, J.; Geib, S. V.; Lin, C.-H. Heterocycles 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron: Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573. Katsumata, A.; Iwaki, T.; Fukumoto, K.; Ihara, M. Heterocycles 1997, 46, 605. Lee, E.; Jeong, J.-W.; Yu, Y. Tetrahedron Lett. 1997, 38, 7765.
18. Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276. Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489. Ishibashi, H.; Kodama, K.; Kameoka, C.; Kawanami, H.; Ikeda, M. Tetrahedron 1996, 52, 13867. Ishibashi, H.; Kawanami, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 817. Ishibashi, H.; Kameoka, C.; Kodama, K.; Kawanami, H.; Hamada, M.; Ikeda, M. Tetrahedron 1997, 53, 9611.
19. Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276. Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489. Ishibashi, H.; Kodama, K.; Kameoka, C.; Kawanami, H.; Ikeda, M. Tetrahedron 1996, 52, 13867. Ishibashi, H.; Kawanami, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 817. Ishibashi, H.; Kameoka, C.; Kodama, K.; Kawanami, H.; Hamada, M.; Ikeda, M. Tetrahedron 1997, 53, 9611.
20. Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276. Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489. Ishibashi, H.; Kodama, K.; Kameoka, C.; Kawanami, H.; Ikeda, M. Tetrahedron 1996, 52, 13867. Ishibashi, H.; Kawanami, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 817. Ishibashi, H.; Kameoka, C.; Kodama, K.; Kawanami, H.; Hamada, M.; Ikeda, M. Tetrahedron 1997, 53, 9611.
21. Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276. Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489. Ishibashi, H.; Kodama, K.; Kameoka, C.; Kawanami, H.; Ikeda, M. Tetrahedron 1996, 52, 13867. Ishibashi, H.; Kawanami, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 817. Ishibashi, H.; Kameoka, C.; Kodama, K.; Kawanami, H.; Hamada, M.; Ikeda, M. Tetrahedron 1997, 53, 9611.
22. Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276. Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489. Ishibashi, H.; Kodama, K.; Kameoka, C.; Kawanami, H.; Ikeda, M. Tetrahedron 1996, 52, 13867. Ishibashi, H.; Kawanami, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 817. Ishibashi, H.; Kameoka, C.; Kodama, K.; Kawanami, H.; Hamada, M.; Ikeda, M. Tetrahedron 1997, 53, 9611.
23. Ishibashi, H.; Fuke, Y.; Yamashita, T.; Ikeda, M. Tetrahedron: Asymmetry 1996, 7, 2531.
24. Absolute configuration of 2a and 2b was deduced from the results with the N-[(S)-1-(1-naphthyl)ethyl] congener of 1, which gave the corresponding (3aR,7aR)-octahydroindol-2-one as the major product.
25. Viehe, H. G.; Merenyi, R.; Stella, L.; Janousek, Z. Angew. Chem., Int. Ed. Engl. 1979, 18, 917.
26. For a review, see: Martin, S. F. In The Alkaloids; Brossi, A. Ed.; Academic: New York, 1987; Vol. 30, pp 251-376.
27. Kotera, K. Tetrahedron 1961, 12, 248.
28. For recent syntheses of racemic γ-lycorane, see: Bäckvall, J.-E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1995, 36, 6185.
29. For recent syntheses of racemic γ-lycorane, see: Bäckvall, J.-E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1995, 36, 6185.
30. For recent syntheses of racemic γ-lycorane, see: Bäckvall, J.-E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1995, 36, 6185.
31. For recent syntheses of racemic γ-lycorane, see: Bäckvall, J.-E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1995, 36, 6185.
32. For recent syntheses of racemic γ-lycorane, see: Bäckvall, J.-E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1995, 36, 6185.
33. Synthesis of (+)-γ-lycorane has been reported by Mori and co-workers. See: Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016.
34. Martin, J. C.; Arhart, R. J. J. Am. Chem. Soc. 1971, 93, 2341. For a recent example of the use of Martin sulfurane in total synthesis, see: Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am. Chem. Soc. 1997, 119, 8438.
35. Martin, J. C.; Arhart, R. J. J. Am. Chem. Soc. 1971, 93, 2341. For a recent example of the use of Martin sulfurane in total synthesis, see: Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. J. Am. Chem. Soc. 1997, 119, 8438.