Total synthesis of (±)-α- and β-lycoranes by sequential chemoselective conjugate addition-stereoselective nitro-Michael cyclization of an ω-nitro-α,β,ψ,ω-unsaturated ester

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1123-1126

  Yasuhara, Tomohisa ^a   Nishimura, Katsumi ^b   Yamashita, Mitsuaki ^b   Fukuyama, Naoshi ^b   Yamada, Ken Ichi ^b   Muraoka, Osamu ^a   Tomioka, Kiyoshi ^b  

^a KINKI UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; ALKENE DERIVATIVE; ALPHA LYCORANE; BETA LYCORANE; HEXANE; LITHIUM DERIVATIVE; LYCORINE; NITRO DERIVATIVE; UNCLASSIFIED DRUG; ALKALOID; AMARYLLIDACEAE ALKALOID; ESTER; LYCORANE; NITROGEN;

ARTICLE; CONJUGATE; CYCLIZATION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STEREOCHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AMARYLLIDACEAE ALKALOIDS; CYCLIZATION; ESTERS; MOLECULAR STRUCTURE; NITROGEN; STEREOISOMERISM;

EID: 0042730091     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0341905     Document Type: Article

References (83)

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11. Synthesis of 3: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933-934. (b) Møller, O.; Steinberg, E.-M.; Torssell, K. Acta Chem. Scand., Sect. B 1978, 32, 98-104. (c) Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K. Heterocycles 1979, 12, 1475-1478. (d) Sano, T.; Kashiwaba, N.; Tada, J.; Tsuda, Y.; Irie, H. Heterocycles 1980, 32, 1097-1100. (e) Martin, S. F.; Tu, C.; Kimura, M.; Simonsen, S. H. J. Org. Chem. 1982, 47, 3634-3643. (f) Boeckman, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250-8252. (g) Umezawa, B.; Hoshino, O.; Sawaki, H.; Mori, K.; Hamada, Y.; Kotera, K.; Iitaka, Y. Tetrahedron 1984, 40, 1783-1790. (h) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210-6219. (i) Hoshino, O.; Ishizaki, M.; Kamei, K.; Taguchi, M.; Nagao, T.; Iwaoka, K.; Sawai, S.; Umezawa, B.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 1 1996, 571-580.
12. Synthesis of 3: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933-934. (b) Møller, O.; Steinberg, E.-M.; Torssell, K. Acta Chem. Scand., Sect. B 1978, 32, 98-104. (c) Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K. Heterocycles 1979, 12, 1475-1478. (d) Sano, T.; Kashiwaba, N.; Tada, J.; Tsuda, Y.; Irie, H. Heterocycles 1980, 32, 1097-1100. (e) Martin, S. F.; Tu, C.; Kimura, M.; Simonsen, S. H. J. Org. Chem. 1982, 47, 3634-3643. (f) Boeckman, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250-8252. (g) Umezawa, B.; Hoshino, O.; Sawaki, H.; Mori, K.; Hamada, Y.; Kotera, K.; Iitaka, Y. Tetrahedron 1984, 40, 1783-1790. (h) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210-6219. (i) Hoshino, O.; Ishizaki, M.; Kamei, K.; Taguchi, M.; Nagao, T.; Iwaoka, K.; Sawai, S.; Umezawa, B.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 1 1996, 571-580.
13. Synthesis of 3: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933-934. (b) Møller, O.; Steinberg, E.-M.; Torssell, K. Acta Chem. Scand., Sect. B 1978, 32, 98-104. (c) Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K. Heterocycles 1979, 12, 1475-1478. (d) Sano, T.; Kashiwaba, N.; Tada, J.; Tsuda, Y.; Irie, H. Heterocycles 1980, 32, 1097-1100. (e) Martin, S. F.; Tu, C.; Kimura, M.; Simonsen, S. H. J. Org. Chem. 1982, 47, 3634-3643. (f) Boeckman, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250-8252. (g) Umezawa, B.; Hoshino, O.; Sawaki, H.; Mori, K.; Hamada, Y.; Kotera, K.; Iitaka, Y. Tetrahedron 1984, 40, 1783-1790. (h) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210-6219. (i) Hoshino, O.; Ishizaki, M.; Kamei, K.; Taguchi, M.; Nagao, T.; Iwaoka, K.; Sawai, S.; Umezawa, B.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 1 1996, 571-580.
14. Synthesis of 3: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933-934. (b) Møller, O.; Steinberg, E.-M.; Torssell, K. Acta Chem. Scand., Sect. B 1978, 32, 98-104. (c) Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K. Heterocycles 1979, 12, 1475-1478. (d) Sano, T.; Kashiwaba, N.; Tada, J.; Tsuda, Y.; Irie, H. Heterocycles 1980, 32, 1097-1100. (e) Martin, S. F.; Tu, C.; Kimura, M.; Simonsen, S. H. J. Org. Chem. 1982, 47, 3634-3643. (f) Boeckman, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250-8252. (g) Umezawa, B.; Hoshino, O.; Sawaki, H.; Mori, K.; Hamada, Y.; Kotera, K.; Iitaka, Y. Tetrahedron 1984, 40, 1783-1790. (h) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210-6219. (i) Hoshino, O.; Ishizaki, M.; Kamei, K.; Taguchi, M.; Nagao, T.; Iwaoka, K.; Sawai, S.; Umezawa, B.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 1 1996, 571-580.
15. Synthesis of 3: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933-934. (b) Møller, O.; Steinberg, E.-M.; Torssell, K. Acta Chem. Scand., Sect. B 1978, 32, 98-104. (c) Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K. Heterocycles 1979, 12, 1475-1478. (d) Sano, T.; Kashiwaba, N.; Tada, J.; Tsuda, Y.; Irie, H. Heterocycles 1980, 32, 1097-1100. (e) Martin, S. F.; Tu, C.; Kimura, M.; Simonsen, S. H. J. Org. Chem. 1982, 47, 3634-3643. (f) Boeckman, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250-8252. (g) Umezawa, B.; Hoshino, O.; Sawaki, H.; Mori, K.; Hamada, Y.; Kotera, K.; Iitaka, Y. Tetrahedron 1984, 40, 1783-1790. (h) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210-6219. (i) Hoshino, O.; Ishizaki, M.; Kamei, K.; Taguchi, M.; Nagao, T.; Iwaoka, K.; Sawai, S.; Umezawa, B.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 1 1996, 571-580.
16. Synthesis of 3: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933-934. (b) Møller, O.; Steinberg, E.-M.; Torssell, K. Acta Chem. Scand., Sect. B 1978, 32, 98-104. (c) Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K. Heterocycles 1979, 12, 1475-1478. (d) Sano, T.; Kashiwaba, N.; Tada, J.; Tsuda, Y.; Irie, H. Heterocycles 1980, 32, 1097-1100. (e) Martin, S. F.; Tu, C.; Kimura, M.; Simonsen, S. H. J. Org. Chem. 1982, 47, 3634-3643. (f) Boeckman, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250-8252. (g) Umezawa, B.; Hoshino, O.; Sawaki, H.; Mori, K.; Hamada, Y.; Kotera, K.; Iitaka, Y. Tetrahedron 1984, 40, 1783-1790. (h) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210-6219. (i) Hoshino, O.; Ishizaki, M.; Kamei, K.; Taguchi, M.; Nagao, T.; Iwaoka, K.; Sawai, S.; Umezawa, B.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 1 1996, 571-580.
17. Synthesis of 3: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933-934. (b) Møller, O.; Steinberg, E.-M.; Torssell, K. Acta Chem. Scand., Sect. B 1978, 32, 98-104. (c) Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K. Heterocycles 1979, 12, 1475-1478. (d) Sano, T.; Kashiwaba, N.; Tada, J.; Tsuda, Y.; Irie, H. Heterocycles 1980, 32, 1097-1100. (e) Martin, S. F.; Tu, C.; Kimura, M.; Simonsen, S. H. J. Org. Chem. 1982, 47, 3634-3643. (f) Boeckman, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250-8252. (g) Umezawa, B.; Hoshino, O.; Sawaki, H.; Mori, K.; Hamada, Y.; Kotera, K.; Iitaka, Y. Tetrahedron 1984, 40, 1783-1790. (h) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210-6219. (i) Hoshino, O.; Ishizaki, M.; Kamei, K.; Taguchi, M.; Nagao, T.; Iwaoka, K.; Sawai, S.; Umezawa, B.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 1 1996, 571-580.
18. Synthesis of 3: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933-934. (b) Møller, O.; Steinberg, E.-M.; Torssell, K. Acta Chem. Scand., Sect. B 1978, 32, 98-104. (c) Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K. Heterocycles 1979, 12, 1475-1478. (d) Sano, T.; Kashiwaba, N.; Tada, J.; Tsuda, Y.; Irie, H. Heterocycles 1980, 32, 1097-1100. (e) Martin, S. F.; Tu, C.; Kimura, M.; Simonsen, S. H. J. Org. Chem. 1982, 47, 3634-3643. (f) Boeckman, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250-8252. (g) Umezawa, B.; Hoshino, O.; Sawaki, H.; Mori, K.; Hamada, Y.; Kotera, K.; Iitaka, Y. Tetrahedron 1984, 40, 1783-1790. (h) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210-6219. (i) Hoshino, O.; Ishizaki, M.; Kamei, K.; Taguchi, M.; Nagao, T.; Iwaoka, K.; Sawai, S.; Umezawa, B.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 1 1996, 571-580.
19. Synthesis of 3: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933-934. (b) Møller, O.; Steinberg, E.-M.; Torssell, K. Acta Chem. Scand., Sect. B 1978, 32, 98-104. (c) Umezawa, B.; Hoshino, O.; Sawaki, S.; Sashida, H.; Mori, K. Heterocycles 1979, 12, 1475-1478. (d) Sano, T.; Kashiwaba, N.; Tada, J.; Tsuda, Y.; Irie, H. Heterocycles 1980, 32, 1097-1100. (e) Martin, S. F.; Tu, C.; Kimura, M.; Simonsen, S. H. J. Org. Chem. 1982, 47, 3634-3643. (f) Boeckman, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250-8252. (g) Umezawa, B.; Hoshino, O.; Sawaki, H.; Mori, K.; Hamada, Y.; Kotera, K.; Iitaka, Y. Tetrahedron 1984, 40, 1783-1790. (h) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210-6219. (i) Hoshino, O.; Ishizaki, M.; Kamei, K.; Taguchi, M.; Nagao, T.; Iwaoka, K.; Sawai, S.; Umezawa, B.; Iitaka, Y. J. Chem. Soc., Perkin Trans. 1 1996, 571-580.
20. Synthesis of 1: (a) Hill, R. K.; Joule, J. A.; Loerrler, L. J. J. Am. Chem. Soc. 1962, 84, 1-4956. (b) Umezawa, B.; Hoshino, O.; Sawaki, S. Sato, S.; Numao, N. J. Org. Chem. 1977, 26, 4272-4275. (c) Tanaka, H.; Nagai, Y.; Irie, H.; Uyeo, S.; Kuno, A. J. Chem. Soc., Perkin Trans. 1 1979, 874-878. (d) Wang, C.-L. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613-4616. (e) Bäckwell, J.-E.; Anderson, G. B. S.; Goggoll, A. J. Org. Chem. 1991, 56, 2988-2993. (f) Oppolzer, W.; Spivey, A. C.; Bochet, C. G. J. Am. Chem. Soc. 1994, 116, 3139-3140. (g) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569-10582. (h) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135-1138. (i) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545. See also ref 5e.
21. Synthesis of 1: (a) Hill, R. K.; Joule, J. A.; Loerrler, L. J. J. Am. Chem. Soc. 1962, 84, 1-4956. (b) Umezawa, B.; Hoshino, O.; Sawaki, S. Sato, S.; Numao, N. J. Org. Chem. 1977, 26, 4272-4275. (c) Tanaka, H.; Nagai, Y.; Irie, H.; Uyeo, S.; Kuno, A. J. Chem. Soc., Perkin Trans. 1 1979, 874-878. (d) Wang, C.-L. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613-4616. (e) Bäckwell, J.-E.; Anderson, G. B. S.; Goggoll, A. J. Org. Chem. 1991, 56, 2988-2993. (f) Oppolzer, W.; Spivey, A. C.; Bochet, C. G. J. Am. Chem. Soc. 1994, 116, 3139-3140. (g) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569-10582. (h) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135-1138. (i) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545. See also ref 5e.
22. Synthesis of 1: (a) Hill, R. K.; Joule, J. A.; Loerrler, L. J. J. Am. Chem. Soc. 1962, 84, 1-4956. (b) Umezawa, B.; Hoshino, O.; Sawaki, S. Sato, S.; Numao, N. J. Org. Chem. 1977, 26, 4272-4275. (c) Tanaka, H.; Nagai, Y.; Irie, H.; Uyeo, S.; Kuno, A. J. Chem. Soc., Perkin Trans. 1 1979, 874-878. (d) Wang, C.-L. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613-4616. (e) Bäckwell, J.-E.; Anderson, G. B. S.; Goggoll, A. J. Org. Chem. 1991, 56, 2988-2993. (f) Oppolzer, W.; Spivey, A. C.; Bochet, C. G. J. Am. Chem. Soc. 1994, 116, 3139-3140. (g) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569-10582. (h) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135-1138. (i) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545. See also ref 5e.
23. Synthesis of 1: (a) Hill, R. K.; Joule, J. A.; Loerrler, L. J. J. Am. Chem. Soc. 1962, 84, 1-4956. (b) Umezawa, B.; Hoshino, O.; Sawaki, S. Sato, S.; Numao, N. J. Org. Chem. 1977, 26, 4272-4275. (c) Tanaka, H.; Nagai, Y.; Irie, H.; Uyeo, S.; Kuno, A. J. Chem. Soc., Perkin Trans. 1 1979, 874-878. (d) Wang, C.-L. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613-4616. (e) Bäckwell, J.-E.; Anderson, G. B. S.; Goggoll, A. J. Org. Chem. 1991, 56, 2988-2993. (f) Oppolzer, W.; Spivey, A. C.; Bochet, C. G. J. Am. Chem. Soc. 1994, 116, 3139-3140. (g) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569-10582. (h) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135-1138. (i) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545. See also ref 5e.
24. Synthesis of 1: (a) Hill, R. K.; Joule, J. A.; Loerrler, L. J. J. Am. Chem. Soc. 1962, 84, 1-4956. (b) Umezawa, B.; Hoshino, O.; Sawaki, S. Sato, S.; Numao, N. J. Org. Chem. 1977, 26, 4272-4275. (c) Tanaka, H.; Nagai, Y.; Irie, H.; Uyeo, S.; Kuno, A. J. Chem. Soc., Perkin Trans. 1 1979, 874-878. (d) Wang, C.-L. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613-4616. (e) Bäckwell, J.-E.; Anderson, G. B. S.; Goggoll, A. J. Org. Chem. 1991, 56, 2988-2993. (f) Oppolzer, W.; Spivey, A. C.; Bochet, C. G. J. Am. Chem. Soc. 1994, 116, 3139-3140. (g) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569-10582. (h) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135-1138. (i) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545. See also ref 5e.
25. Synthesis of 1: (a) Hill, R. K.; Joule, J. A.; Loerrler, L. J. J. Am. Chem. Soc. 1962, 84, 1-4956. (b) Umezawa, B.; Hoshino, O.; Sawaki, S. Sato, S.; Numao, N. J. Org. Chem. 1977, 26, 4272-4275. (c) Tanaka, H.; Nagai, Y.; Irie, H.; Uyeo, S.; Kuno, A. J. Chem. Soc., Perkin Trans. 1 1979, 874-878. (d) Wang, C.-L. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613-4616. (e) Bäckwell, J.-E.; Anderson, G. B. S.; Goggoll, A. J. Org. Chem. 1991, 56, 2988-2993. (f) Oppolzer, W.; Spivey, A. C.; Bochet, C. G. J. Am. Chem. Soc. 1994, 116, 3139-3140. (g) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569-10582. (h) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135-1138. (i) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545. See also ref 5e.
26. Synthesis of 1: (a) Hill, R. K.; Joule, J. A.; Loerrler, L. J. J. Am. Chem. Soc. 1962, 84, 1-4956. (b) Umezawa, B.; Hoshino, O.; Sawaki, S. Sato, S.; Numao, N. J. Org. Chem. 1977, 26, 4272-4275. (c) Tanaka, H.; Nagai, Y.; Irie, H.; Uyeo, S.; Kuno, A. J. Chem. Soc., Perkin Trans. 1 1979, 874-878. (d) Wang, C.-L. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613-4616. (e) Bäckwell, J.-E.; Anderson, G. B. S.; Goggoll, A. J. Org. Chem. 1991, 56, 2988-2993. (f) Oppolzer, W.; Spivey, A. C.; Bochet, C. G. J. Am. Chem. Soc. 1994, 116, 3139-3140. (g) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569-10582. (h) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135-1138. (i) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545. See also ref 5e.
27. Synthesis of 1: (a) Hill, R. K.; Joule, J. A.; Loerrler, L. J. J. Am. Chem. Soc. 1962, 84, 1-4956. (b) Umezawa, B.; Hoshino, O.; Sawaki, S. Sato, S.; Numao, N. J. Org. Chem. 1977, 26, 4272-4275. (c) Tanaka, H.; Nagai, Y.; Irie, H.; Uyeo, S.; Kuno, A. J. Chem. Soc., Perkin Trans. 1 1979, 874-878. (d) Wang, C.-L. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613-4616. (e) Bäckwell, J.-E.; Anderson, G. B. S.; Goggoll, A. J. Org. Chem. 1991, 56, 2988-2993. (f) Oppolzer, W.; Spivey, A. C.; Bochet, C. G. J. Am. Chem. Soc. 1994, 116, 3139-3140. (g) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569-10582. (h) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135-1138. (i) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545. See also ref 5e.
28. Synthesis of 1: (a) Hill, R. K.; Joule, J. A.; Loerrler, L. J. J. Am. Chem. Soc. 1962, 84, 1-4956. (b) Umezawa, B.; Hoshino, O.; Sawaki, S. Sato, S.; Numao, N. J. Org. Chem. 1977, 26, 4272-4275. (c) Tanaka, H.; Nagai, Y.; Irie, H.; Uyeo, S.; Kuno, A. J. Chem. Soc., Perkin Trans. 1 1979, 874-878. (d) Wang, C.-L. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613-4616. (e) Bäckwell, J.-E.; Anderson, G. B. S.; Goggoll, A. J. Org. Chem. 1991, 56, 2988-2993. (f) Oppolzer, W.; Spivey, A. C.; Bochet, C. G. J. Am. Chem. Soc. 1994, 116, 3139-3140. (g) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569-10582. (h) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135-1138. (i) Tamura, O.; Matsukida, H.; Toyao, A.; Takeda, Y.; Ishibashi, H. J. Org. Chem. 2002, 67, 5537-5545. See also ref 5e.
29. Synthesis of 2: see refs 5e, 6a, and 6c.
30. Recent synthesis of γ-lycorane: (a) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016-2021. (b) Cossy, J.; Tresnard, L.; Pard, D. G. Eur. J. Org. Chem. 1999, 1925, 5-1933. (c) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716-1724.
31. Recent synthesis of γ-lycorane: (a) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016-2021. (b) Cossy, J.; Tresnard, L.; Pard, D. G. Eur. J. Org. Chem. 1999, 1925, 5-1933. (c) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716-1724.
32. Recent synthesis of γ-lycorane: (a) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016-2021. (b) Cossy, J.; Tresnard, L.; Pard, D. G. Eur. J. Org. Chem. 1999, 1925, 5-1933. (c) Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716-1724.
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50. (a) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975.
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53. (d) Nishimura, K.; Tomioka, K. Yakugaku Zasshi 2003, 123, 9-18.
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56. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
57. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
58. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
59. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
60. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
61. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
62. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
63. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
64. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
65. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
66. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
67. Conjugate addition of nitroalkene: (a) Seebach, D.; Crass, G.; Wilka, E.-M.; Hilvert, D.; Brunner, E. Helv. Chem. Acta 1979, 62, 2695-2698. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324. (c) Sewald, N.; Wendish, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (d) Versleijer, J. P. G. ; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (f) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (g) Johnson, T. A. ; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (h) Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (i) Luchaco-cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (j) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698. (k) Rimkus, A.; Sewald, N. Org. Lett. 2002, 4, 3289-3291. (l) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
68. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
69. Nitro-Michael addition: (a) Baum, K.; Guest, A. M. Synthesis 1979, 311-312. (b) Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1980, 19, 1046-1051. (c) Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226-227. (d) Bergbreiter, D. E.; Lalonde, J. J. J. Org. Chem. 1987, 52, 1601-1603. (e) Ballini, R.; Bosica, G. Tetrahedron Lett. 1996, 37, 8027-8030. (f) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259. (g) Kisanga, P. B.; Ilankumaran, P.; Fetterly, B. M.; Verkade, J. G. J. Org. Chem. 2002, 67, 3555-3560.
70. Nitro-Michael addition: (a) Baum, K.; Guest, A. M. Synthesis 1979, 311-312. (b) Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1980, 19, 1046-1051. (c) Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226-227. (d) Bergbreiter, D. E.; Lalonde, J. J. J. Org. Chem. 1987, 52, 1601-1603. (e) Ballini, R.; Bosica, G. Tetrahedron Lett. 1996, 37, 8027-8030. (f) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259. (g) Kisanga, P. B.; Ilankumaran, P.; Fetterly, B. M.; Verkade, J. G. J. Org. Chem. 2002, 67, 3555-3560.
71. Nitro-Michael addition: (a) Baum, K.; Guest, A. M. Synthesis 1979, 311-312. (b) Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1980, 19, 1046-1051. (c) Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226-227. (d) Bergbreiter, D. E.; Lalonde, J. J. J. Org. Chem. 1987, 52, 1601-1603. (e) Ballini, R.; Bosica, G. Tetrahedron Lett. 1996, 37, 8027-8030. (f) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259. (g) Kisanga, P. B.; Ilankumaran, P.; Fetterly, B. M.; Verkade, J. G. J. Org. Chem. 2002, 67, 3555-3560.
72. Nitro-Michael addition: (a) Baum, K.; Guest, A. M. Synthesis 1979, 311-312. (b) Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1980, 19, 1046-1051. (c) Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226-227. (d) Bergbreiter, D. E.; Lalonde, J. J. J. Org. Chem. 1987, 52, 1601-1603. (e) Ballini, R.; Bosica, G. Tetrahedron Lett. 1996, 37, 8027-8030. (f) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259. (g) Kisanga, P. B.; Ilankumaran, P.; Fetterly, B. M.; Verkade, J. G. J. Org. Chem. 2002, 67, 3555-3560.
73. Nitro-Michael addition: (a) Baum, K.; Guest, A. M. Synthesis 1979, 311-312. (b) Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1980, 19, 1046-1051. (c) Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226-227. (d) Bergbreiter, D. E.; Lalonde, J. J. J. Org. Chem. 1987, 52, 1601-1603. (e) Ballini, R.; Bosica, G. Tetrahedron Lett. 1996, 37, 8027-8030. (f) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259. (g) Kisanga, P. B.; Ilankumaran, P.; Fetterly, B. M.; Verkade, J. G. J. Org. Chem. 2002, 67, 3555-3560.
74. Nitro-Michael addition: (a) Baum, K.; Guest, A. M. Synthesis 1979, 311-312. (b) Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1980, 19, 1046-1051. (c) Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226-227. (d) Bergbreiter, D. E.; Lalonde, J. J. J. Org. Chem. 1987, 52, 1601-1603. (e) Ballini, R.; Bosica, G. Tetrahedron Lett. 1996, 37, 8027-8030. (f) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259. (g) Kisanga, P. B.; Ilankumaran, P.; Fetterly, B. M.; Verkade, J. G. J. Org. Chem. 2002, 67, 3555-3560.
75. Nitro-Michael addition: (a) Baum, K.; Guest, A. M. Synthesis 1979, 311-312. (b) Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1980, 19, 1046-1051. (c) Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226-227. (d) Bergbreiter, D. E.; Lalonde, J. J. J. Org. Chem. 1987, 52, 1601-1603. (e) Ballini, R.; Bosica, G. Tetrahedron Lett. 1996, 37, 8027-8030. (f) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257-4259. (g) Kisanga, P. B.; Ilankumaran, P.; Fetterly, B. M.; Verkade, J. G. J. Org. Chem. 2002, 67, 3555-3560.
76. Denmark, S. E.; Senanayake, B. W. J. Org. Chem. 1993, 58, 1835-1858.
77. (a) Kamimura, A.; Sasatani, H.; Hashimoto, T.; Kawai, T.; Hori, K.; Ono, N. J. Org. Chem. 1990, 55, 2437-2442.
78. (b) Hori, K.; Higuchi, S.; Kamimura, A. J. Org. Chem. 1990, 55, 5900-5905.
79. The possibility of thermodynamic control is not excluded.
80. Michaelides, M. R.; Hong, Y.; DiDomenico, S., Jr.; Bayburt, E. K.; Asin, K. E.; Britton, D. R.; Lin, C. W.; Shosaki, K. J. Med. Chem. 1997, 40, 1585-1599.
81. Tomioka, K.; Kubota, Y.; Koga, K. Tetrahedron Lett. 1993, 49, 1891-1900.
82. 5e mp 86-88°C).
83. 5e mp 92-94°C).