Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids

Journal of Organic Chemistry

Volumn 70, Issue 8, 2005, Pages 3157-3167

  Alibés, Ramon ^a   Blanco, Pilar ^a   Casas, Eva ^a   Closa, Montserrat ^a   De March, Pedro ^a   Figueredo, Marta ^a   Font, Josep ^a   Sanfeliu, Elena ^a   Álvarez Larena, Ángel ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; OLEFINS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CYCLIC NITRONES; CYCLOADDITION; DIVERSITY-ORIENTED APPROACH; STEMONA ALKALOIDS;

AROMATIC COMPOUNDS;

1 AZABICYCLO[5.3.0] DECANE; ALKALOID; DECANE; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CONTROLLED STUDY; CRYSTALLIZATION; CYCLOADDITION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; NONHUMAN; PHASE TRANSITION; STEMONACEAE; STEREOCHEMISTRY;

ALKALOIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEMONACEAE;

EID: 17444378245     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047867q     Document Type: Article

References (118)

1. (a) Götz, M.; Edwards, O. E. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol 9, pp 545-551.
2. (b) Götz, M.; Strunz, G. M. In Alkaloids; Wiesner, K., Ed.; MTP International Review of Sciences, Organic Chemistry, Series One; Butterworth: London, 1973; Vol. 9, pp 143-160.
3. Stemofoline, stemonine and stemospironine: (a) Sakata, K.; Aoki, K.; Chang, C.-F.; Sakurai, A.; Tamura, S.; Murakoshi, S. Agric. Biol. Chem. 1978, 42, 457. Tuberostemonine: (b) Terada, M.; Sano, M.; Ishii, A. I.; Kino, H.; Fukushima, S.; Noro, T. Nippon Yakurigaku Zasshi 1982, 79, 93. (c) Shinozaki, H.; Ishida, M. Brain Res. 1985, 334, 33. Neostemonine and isoprotostemonine: (d) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1205. Asparagamine A: (e) Sekine, T.; Ikegami, F.; Fukasawa, N.; Kashiwagi, Y.; Aizawa, T.; Fujii, Y.; Ruangrungsi, N.; Murakoshi, I. J. Chem. Soc., Perkin Trans. 1 1995, 391. Stemofoline: (f) Jiwajinda, S.; Hirai, N.; Watanabe, K.; Santisopasri, V.; Chuengsamarnyart, N.; Koshimizu, K.; Ohigashi, H. Phytochemistry 2001, 56, 693.
4. Stemofoline, stemonine and stemospironine: (a) Sakata, K.; Aoki, K.; Chang, C.-F.; Sakurai, A.; Tamura, S.; Murakoshi, S. Agric. Biol. Chem. 1978, 42, 457. Tuberostemonine: (b) Terada, M.; Sano, M.; Ishii, A. I.; Kino, H.; Fukushima, S.; Noro, T. Nippon Yakurigaku Zasshi 1982, 79, 93. (c) Shinozaki, H.; Ishida, M. Brain Res. 1985, 334, 33. Neostemonine and isoprotostemonine: (d) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1205. Asparagamine A: (e) Sekine, T.; Ikegami, F.; Fukasawa, N.; Kashiwagi, Y.; Aizawa, T.; Fujii, Y.; Ruangrungsi, N.; Murakoshi, I. J. Chem. Soc., Perkin Trans. 1 1995, 391. Stemofoline: (f) Jiwajinda, S.; Hirai, N.; Watanabe, K.; Santisopasri, V.; Chuengsamarnyart, N.; Koshimizu, K.; Ohigashi, H. Phytochemistry 2001, 56, 693.
5. Stemofoline, stemonine and stemospironine: (a) Sakata, K.; Aoki, K.; Chang, C.-F.; Sakurai, A.; Tamura, S.; Murakoshi, S. Agric. Biol. Chem. 1978, 42, 457. Tuberostemonine: (b) Terada, M.; Sano, M.; Ishii, A. I.; Kino, H.; Fukushima, S.; Noro, T. Nippon Yakurigaku Zasshi 1982, 79, 93. (c) Shinozaki, H.; Ishida, M. Brain Res. 1985, 334, 33. Neostemonine and isoprotostemonine: (d) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1205. Asparagamine A: (e) Sekine, T.; Ikegami, F.; Fukasawa, N.; Kashiwagi, Y.; Aizawa, T.; Fujii, Y.; Ruangrungsi, N.; Murakoshi, I. J. Chem. Soc., Perkin Trans. 1 1995, 391. Stemofoline: (f) Jiwajinda, S.; Hirai, N.; Watanabe, K.; Santisopasri, V.; Chuengsamarnyart, N.; Koshimizu, K.; Ohigashi, H. Phytochemistry 2001, 56, 693.
6. Stemofoline, stemonine and stemospironine: (a) Sakata, K.; Aoki, K.; Chang, C.-F.; Sakurai, A.; Tamura, S.; Murakoshi, S. Agric. Biol. Chem. 1978, 42, 457. Tuberostemonine: (b) Terada, M.; Sano, M.; Ishii, A. I.; Kino, H.; Fukushima, S.; Noro, T. Nippon Yakurigaku Zasshi 1982, 79, 93. (c) Shinozaki, H.; Ishida, M. Brain Res. 1985, 334, 33. Neostemonine and isoprotostemonine: (d) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1205. Asparagamine A: (e) Sekine, T.; Ikegami, F.; Fukasawa, N.; Kashiwagi, Y.; Aizawa, T.; Fujii, Y.; Ruangrungsi, N.; Murakoshi, I. J. Chem. Soc., Perkin Trans. 1 1995, 391. Stemofoline: (f) Jiwajinda, S.; Hirai, N.; Watanabe, K.; Santisopasri, V.; Chuengsamarnyart, N.; Koshimizu, K.; Ohigashi, H. Phytochemistry 2001, 56, 693.
7. Stemofoline, stemonine and stemospironine: (a) Sakata, K.; Aoki, K.; Chang, C.-F.; Sakurai, A.; Tamura, S.; Murakoshi, S. Agric. Biol. Chem. 1978, 42, 457. Tuberostemonine: (b) Terada, M.; Sano, M.; Ishii, A. I.; Kino, H.; Fukushima, S.; Noro, T. Nippon Yakurigaku Zasshi 1982, 79, 93. (c) Shinozaki, H.; Ishida, M. Brain Res. 1985, 334, 33. Neostemonine and isoprotostemonine: (d) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1205. Asparagamine A: (e) Sekine, T.; Ikegami, F.; Fukasawa, N.; Kashiwagi, Y.; Aizawa, T.; Fujii, Y.; Ruangrungsi, N.; Murakoshi, I. J. Chem. Soc., Perkin Trans. 1 1995, 391. Stemofoline: (f) Jiwajinda, S.; Hirai, N.; Watanabe, K.; Santisopasri, V.; Chuengsamarnyart, N.; Koshimizu, K.; Ohigashi, H. Phytochemistry 2001, 56, 693.
8. Stemofoline, stemonine and stemospironine: (a) Sakata, K.; Aoki, K.; Chang, C.-F.; Sakurai, A.; Tamura, S.; Murakoshi, S. Agric. Biol. Chem. 1978, 42, 457. Tuberostemonine: (b) Terada, M.; Sano, M.; Ishii, A. I.; Kino, H.; Fukushima, S.; Noro, T. Nippon Yakurigaku Zasshi 1982, 79, 93. (c) Shinozaki, H.; Ishida, M. Brain Res. 1985, 334, 33. Neostemonine and isoprotostemonine: (d) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1205. Asparagamine A: (e) Sekine, T.; Ikegami, F.; Fukasawa, N.; Kashiwagi, Y.; Aizawa, T.; Fujii, Y.; Ruangrungsi, N.; Murakoshi, I. J. Chem. Soc., Perkin Trans. 1 1995, 391. Stemofoline: (f) Jiwajinda, S.; Hirai, N.; Watanabe, K.; Santisopasri, V.; Chuengsamarnyart, N.; Koshimizu, K.; Ohigashi, H. Phytochemistry 2001, 56, 693.
9. For a recent review, see: (a) Pilli, R. A.; Ferreira de Oliveira, M. C. Nat. Prod. Rep. 2000, 17, 117.
10. Harada, H.; Irie, H.; Masaki, N.; Osaki, K.; Uyeo, S. J. Chem. Soc., Chem. Commun. 1967, 460.
11. Huber, C. P.; Hall, S. R.; Maslen, E. N. Tetrahedron Lett. 1968, 4081.
12. Koyama, H.; Oda, K. J. Chem. Soc. B 1970, 1330.
13. Irie, H.; Harada, H.; Ohno, K.; Mizutani, T.; Uyeo, S. J. Chem. Soc., Chem. Commun. 1970, 268.
14. Irie, H.; Masaki, N.; Ohno, K.; Osaki, K.; Taga, T.; Uyeo, S. J. Chem. Soc., Chem. Commun. 1970, 1066.
15. Iizuka, H.; Irie, H.; Masaki, N.; Osaki, K.; Uyeo, S. J. Chem. Soc., Chem. Commun. 1973, 125.
16. Sakata, K.; Aoki, K.; Chang, C.-F.; Sakurai, A.; Tamura, S.; Murakoshi, S. Agric. Biol. Chem. 1978, 42, 457.
17. Noro, T.; Fukushima, S.; Ueno, A.; Miyase, T.; Iitaka, Y.; Saiki, Y. Chem. Pharm. Bull. 1979, 27, 1495.
18. Lin, W.; Xu, R.-S.; Wang, R.; Mak, T. C. W. J. Crystall. Spectrosc. Res. 1991, 21, 189.
19. Lin, W.-H.; Wang, L.; Quiao, L.; Cai, M. S. Chin. Chem. Lett. 1993, 4, 1067.
20. Also named stemonine LG and neotuberostemonine. Ngoan Dao, C.; Luger, P.; Thanh Ky, P.; Ngoc Kim, V.; Xuan Dung, N. Acta Crystallogr. Sect. C 1994, C50, 1612.
21. Cong, X.; Zhao, H.; Guillaume, D.; Xu, G.; Lu, Y.; Zheng, Q. Phytochemistry 1995, 40, 615.
22. Jiang, R.-W.; Hon, P.-M.; But, P. P.-H.; Chung, H.-S.; Lin, G.; Ye, W.-C.; Mak, T. C. W. Tetrahedron 2002, 58, 6705.
23. Mungkornasawakul, P.; Pyne, S. G.; Jatisatienr, A.; Supyen, D.; Lie, W.; Ung, A. T.; Skelton, B. W.; White, A. H. J. Nat. Prod. 2003, 66, 980.
24. Kaltenegger, E.; Brem, B.; Mereiter, K.; Kalchhauser, H.; Kählig, H.; Hofer, O.; Vajrodaya, S.; Greger, H. Phytochemistry 2003, 63, 803.
25. Kakuta, D.; Hitotsuyanagi, Y.; Matsuura, N.; Fukaya, H.; Takeya, K. Tetrahedron 2003, 59, 7779.
26. Seger, C.; Mereiter, K.; Kaltenegger, E.; Pacher, T.; Greger, H.; Hofer, O. Chem. Biodiversity 2004, 1, 265. Also named asparagamine A: ref 2e.
27. Mungkornasawakul, P.; Pyne, S. G.; Jatisatienr, A.; Supyen, D.; Jatisatienr, C.; Lie, W.; Ung, A. T.; Skelton, B. W.; White, A. H. J. Nat. Prod. 2004, 67, 675.
28. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
29. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
30. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
31. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
32. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
33. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
34. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
35. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
36. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
37. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
38. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
39. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
40. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
41. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
42. Stenine: ref 4. Isostemonamine: ref 9. Stemonacetal, stemonal, and stemonone: (a) Shiengthong, D.; Donavanik, T.; Uaprasert, V.; Roengsumran, S.; Massy-Westropp, R. A. Tetrahedron Lett. 1974, 15, 2015. Stemonidine: (b) Xu, R.-S.; Lu, Y.-J.; Chu, J.-H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667. (c) He, X.; Lin, W.; Xu, R.-S. Huaxue Xuebao 1990, 48, 694. Stemotinine and isostemotinine: ref 22b. Stemoninine: (d) Cheng, D.; Guo, J.; Chu, T. T.; Röder, E. J. Nat. Prod. 1988, 51, 202. Parvistemonine: (e) Lin, W.; Yin, B.; Tang, Z.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1990, 48, 811. Oxymaistemonine: (f) Lin, W.; Ye, Y.; Xu, R.-S. Chin. Chem. Lett. 1991, 2, 369. Parvistemoamide, parvistemoline, and didehydroparvistemonine: (g) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 927. Oxystemofoline and methoxystemofoline: (h) Lin, W.; Xu, R.-S.; Zhong, Q. Huaxue Xuebao 1991, 49, 1034. Tuberostemonol, stemoamide, didehydrotuberostemonine, and tuberostemospironine: (i) Lin, W.-H.; Ye, Y.; Xu, R.-S. J. Nat. Prod. 1992, 55, 571. Didehydroprotostemonine, isoprotostemonine, neostemonine, and stemodiol: (j) Ye, Y.; Xu, R.-S.; Chin. Chem. Lett. 1992, 3, 511. Stemonamide and isostemonamide: (k) Ye, Y.; Qin, G.-W,; Xu, R.-S. J. Nat. Prod. 1994, 57, 665. Neotuberostemonine and bisdehydroneotuberostemonine: (l) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1201. Bisdehydroneostemonine: ref 2d. Tuberostemoenone, N-oxytuberostemonine, and isodidehydrotuberostemonine: (m) Lin, W.; Fu, H. J. Chin. Pharm. Sci. 1999, 8, 1. Tuberostemonine B, tuberostemonine C, bisdehydrotuberostemonine B, bisdehydrotuberostemonine C, and isomaistemonine: (n) Zou, C.; Fu, H.; Lei, H.; Li, J.; Lin, W. J. Chin. Pharm. Sci. 1999, 8, 185. Didehydrocroomine, parvistemoninine, and parvistemoninol: ref 3. Didehydrostemonine: (o) Zou, C.; Li, J.; Lei, H.; Fu, H.; Lin, W. J. Chin. Pharm. Sci. 2000, 9, 113. Stemofoline (two isomers): ref 2f.
43. (+)-Croomme: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1998, 118, 3299. (c) Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am. Chem. Soc. 1999, 121, 6990.
44. (+)-Croomme: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1998, 118, 3299. (c) Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am. Chem. Soc. 1999, 121, 6990.
45. (+)-Croomme: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1998, 118, 3299. (c) Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am. Chem. Soc. 1999, 121, 6990.
46. (±)-Stenine: (a) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (c) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515. (d) Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316. (-)-Stenine: (e) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. (f) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1998, 35, 904. (g) Morimoto, Y.; Iwahashi, M.; Kinoshita, T.; Nishida, K. Chem. - Eur. J. 2001, 7, 4107.
47. (±)-Stenine: (a) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (c) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515. (d) Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316. (-)-Stenine: (e) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. (f) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1998, 35, 904. (g) Morimoto, Y.; Iwahashi, M.; Kinoshita, T.; Nishida, K. Chem. - Eur. J. 2001, 7, 4107.
48. (±)-Stenine: (a) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (c) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515. (d) Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316. (-)-Stenine: (e) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. (f) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1998, 35, 904. (g) Morimoto, Y.; Iwahashi, M.; Kinoshita, T.; Nishida, K. Chem. - Eur. J. 2001, 7, 4107.
49. (±)-Stenine: (a) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (c) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515. (d) Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316. (-)-Stenine: (e) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. (f) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1998, 35, 904. (g) Morimoto, Y.; Iwahashi, M.; Kinoshita, T.; Nishida, K. Chem. - Eur. J. 2001, 7, 4107.
50. (±)-Stenine: (a) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (c) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515. (d) Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316. (-)-Stenine: (e) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. (f) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1998, 35, 904. (g) Morimoto, Y.; Iwahashi, M.; Kinoshita, T.; Nishida, K. Chem. - Eur. J. 2001, 7, 4107.
51. (±)-Stenine: (a) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (c) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515. (d) Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316. (-)-Stenine: (e) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. (f) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1998, 35, 904. (g) Morimoto, Y.; Iwahashi, M.; Kinoshita, T.; Nishida, K. Chem. - Eur. J. 2001, 7, 4107.
52. (±)-Stenine: (a) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1990, 55, 6236. (b) Chen, C.-Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (c) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515. (d) Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316. (-)-Stenine: (e) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106. (f) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1998, 35, 904. (g) Morimoto, Y.; Iwahashi, M.; Kinoshita, T.; Nishida, K. Chem. - Eur. J. 2001, 7, 4107.
53. (±)-Stemoamide: (a) Kohno, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1996, 69, 2063. (b) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409. (-)-Stemoamide: (c) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (d) Kinoshita, A.; Mori, M. J. Org. Chem. 1998, 61, 8356. (e) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287. (f) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 2000, 122, 4295. (g) Gurjar, M. K.; Reddy, D. S. Tetrahedron Lett. 2002, 43, 295.
54. (±)-Stemoamide: (a) Kohno, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1996, 69, 2063. (b) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409. (-)-Stemoamide: (c) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (d) Kinoshita, A.; Mori, M. J. Org. Chem. 1998, 61, 8356. (e) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287. (f) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 2000, 122, 4295. (g) Gurjar, M. K.; Reddy, D. S. Tetrahedron Lett. 2002, 43, 295.
55. (±)-Stemoamide: (a) Kohno, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1996, 69, 2063. (b) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409. (-)-Stemoamide: (c) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (d) Kinoshita, A.; Mori, M. J. Org. Chem. 1998, 61, 8356. (e) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287. (f) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 2000, 122, 4295. (g) Gurjar, M. K.; Reddy, D. S. Tetrahedron Lett. 2002, 43, 295.
56. (±)-Stemoamide: (a) Kohno, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1996, 69, 2063. (b) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409. (-)-Stemoamide: (c) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (d) Kinoshita, A.; Mori, M. J. Org. Chem. 1998, 61, 8356. (e) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287. (f) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 2000, 122, 4295. (g) Gurjar, M. K.; Reddy, D. S. Tetrahedron Lett. 2002, 43, 295.
57. (±)-Stemoamide: (a) Kohno, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1996, 69, 2063. (b) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409. (-)-Stemoamide: (c) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (d) Kinoshita, A.; Mori, M. J. Org. Chem. 1998, 61, 8356. (e) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287. (f) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 2000, 122, 4295. (g) Gurjar, M. K.; Reddy, D. S. Tetrahedron Lett. 2002, 43, 295.
58. (±)-Stemoamide: (a) Kohno, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1996, 69, 2063. (b) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409. (-)-Stemoamide: (c) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (d) Kinoshita, A.; Mori, M. J. Org. Chem. 1998, 61, 8356. (e) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287. (f) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 2000, 122, 4295. (g) Gurjar, M. K.; Reddy, D. S. Tetrahedron Lett. 2002, 43, 295.
59. (±)-Stemoamide: (a) Kohno, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1996, 69, 2063. (b) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409. (-)-Stemoamide: (c) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (d) Kinoshita, A.; Mori, M. J. Org. Chem. 1998, 61, 8356. (e) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287. (f) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 2000, 122, 4295. (g) Gurjar, M. K.; Reddy, D. S. Tetrahedron Lett. 2002, 43, 295.
60. (±)-Isostemofoline: Kende, A. S.; Smalley, T. L., Jr.; Huang, H. J. Am. Chem. Soc. 1999, 121, 7431.
61. (±)-Stemonamide and (±)-isostemonamide: (a) Kende, A. S.; Hernando, J. I. M.; Milbank, J. B. J. Org. Lett. 2001, 3, 2505. (b) Kende, A. S.; Hernando, J. I. M.; Milbank, J. B. J. Tetrahedron 2002, 58, 61.
62. (±)-Stemonamide and (±)-isostemonamide: (a) Kende, A. S.; Hernando, J. I. M.; Milbank, J. B. J. Org. Lett. 2001, 3, 2505. (b) Kende, A. S.; Hernando, J. I. M.; Milbank, J. B. J. Tetrahedron 2002, 58, 61.
63. (-)-Stemospironine: Williams, D. R.; Fromhold, M. G.; Earley, J. D. Org. Lett. 2001, 3, 2721.
64. (-)-Tuberostemonine: Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848.
65. (-)-Stemonine: Williams, D. R.; Shamim, K.; Reddy, J. P.; Amato, G. S.; Shaw, S. M. Org. Lett. 2003, 5, 3361.
66. (±)-Didehydrostemofoline (asparagamine A) and (±)- isodidehydrostemofoline: Brüggemann, M.; McDonald, A. I.; Overman, L. E.; Rosen, M. D.; Schwink, L.; Scott, J. P. J. Am. Chem. Soc. 2003, 125, 15284.
67. Cid, P.; Closa, M.; de March, P.; Figueredo, M.; Font, J.; Sanfeliu, E.; Soria, A. Eur. J. Org. Chem. 2004, 4215.
68. (a) Tufariello, J. J.; Tette, J. P. J. Org. Chem. 1975, 40, 3866.
69. (b) Tufariello, J. J.; Ali, S. A. Tetrahedron Lett. 1979, 20, 4445.
70. (c) Tufariello, J. J. Acc. Chem. Res. 1979, 12, 396.
71. (d) Tufariello, J. J.; Lee, G. E. J. Am. Chem. Soc. 1980, 102, 373.
72. (e) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412.
73. (f) Tufariello, J. J.; Winzenberg, K. Tetrahedron Lett. 1986, 27, 1645.
74. (g) Lathbury, D.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1986, 1017.
75. (h) Cordero, F. M.; Anichini, B.; Goti, A.; Brandi, A. Tetrahedron 1993, 49, 9867.
76. (i) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett 1997, 577.
77. (j) McCaig, A. E.; Meldrum, K. P.; Wightman, R. H. Tetrahedron 1998, 54, 9429.
78. (k) Alibés, R.; Busqué, F.; de March, P.; Figueredo, M.; Font, J. Tetrahedron 1998, 54, 11581.
79. (l) Goti, A.; Cicchi, S.; Cordero, F. M.; Fedi, V.; Brandi, A. Molecules 1999, 4, 1.
80. (m) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585.
81. de March, P.; Figueredo, M.; Font, J. Heterocycles 1999, 50, 1213 and refs therein.
82. (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851.
83. (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316.
84. (c) Oppolzer, W.; Bochet, C. G.; Merifield, E. Tetrahedron Lett. 1994, 35, 7015.
85. (d) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem. 1995, 60, 4743.
86. (e) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1863.
87. (f) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123.
88. (g) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031.
89. (h) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 3489.
90. (i) Closa, M.; Wightman, R. H. Synth. Commun. 1998, 28, 3443.
91. (j) Murahashi, S.-I.; Ohtake, H.; Imada, Y. Tetrahedron Lett. 1998, 39, 2765.
92. (k) Cicchi, S.; Nunes, Jr., J.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 1998, 419.
93. (l) Goti, A.; Cacciarini, M.; Cardona, F.; Brandi, A. Tetrahedron Lett. 1999, 40, 2853.
94. (m) Chiacchio, U.; Corsaro, A.; Gumina, G.; Rescifina, A.; Iannazzo, D.; Piperno, A.; Romeo, G.; Romeo, R. J. Org. Chem. 1999, 64, 9321.
95. (n) Carda, M.; Portolés, R.; Murga, J.; Uriel, S.; Marco, J. A.; Domingo, L. R.; Zaragozá, R. J.; Röper, H. J. Org. Chem. 2000, 65, 7000.
96. (o) Cordero, F. M.; Gensini, M.; Goti, A.; Brandi, A. Org. Lett. 2000, 2, 2475.
97. (p) Busqué, F.; de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. Tetrahedron: Asymmetry 2002, 13, 437.
98. (q) Cordero, F. M.; Pisaneschi, F.; Gensini, M.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 2002, 12, 1941.
99. (r) Alibés, R.; Blanco, P.; de March, P.; Figueredo, M.; Font, J.; Álvarez-Larena, A.; Piniella, J. F. Tetrahedron Lett. 2003, 44, 523.
100. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
101. Büchi, G.; Wüest, H. J. Org. Chem. 1969, 34, 1122.
102. Ashton, W. T.; Canning, L. F.; Reynolds, G. F.; Tolman, R. L.; Karkas, J. D.; Liou, R.; Davies, M.-E. M.; DeWitt, C. M.; Perry, H. C.; Field, A. K. J. Med. Chem. 1985, 28, 926.
103. Mann, J.; Parlett, N. K.; Thomas, A. J. Chem. Res. (S) 1987, 369.
104. The crystal structure of anti-31 has been deposited at the Cambridge Crystallographic Data Centre and was allocated the deposition number CCDC 257171.
105. Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843.
106. For an exhaustive study of the addition of organometallic reagents to 24 see: Mead, K.; Macdonald, T. L. J. Org. Chem. 1985, 50, 422.
107. Alonso-Perarnau, D.; de March, P.; Figueredo, M.; Font, J.; Soria, A. Tetrahedron 1993, 49, 4267.
108. Busqué, F.; de March, P.; Figueredo, M.; Font, J.; Monsalvatje, M.; Virgili, A.; Álvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 1996, 61, 8578.
109. (a) Tufariello, J. J. Chapter 9. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 2.
110. (b) Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis: Novel Strategies in Synthesis; VCH Verlagsgesellschaft: Weinheim, Germany, 1988.
111. (c) Frederickson, M.; Tetrahedron 1907, 53, 403.
112. (d) Bloch, R. Chem. Rev. 1998, 98, 1407.
113. (e) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
114. In a preliminary communication (ref 35r) the relative configuration of this adduct was erroneously assigned as exo.
115. (a) Alderson, T.; Jenner, E. L.; Lindsey, R. V. J. Am. Chem. Soc. 1965, 87, 5638.
116. (b) Nugent, W. A.; Hobbs, F. W., Jr. J. Org. Chem. 1983, 48, 5364.
117. (a) Brown, H. C.; Keblys, K. A. J. Org. Chem. 1966, 31, 485.
118. (b) Huckstep, M.; Taylor, R. J. K. Synthesis 1982, 881.