Benzothiazines in synthesis. Formal syntheses of (+)-curcumene and (+)-curcuphenol

Tetrahedron Letters

Volumn 44, Issue 39, 2003, Pages 7261-7264

  Harmata, Michael ^a   Hong, Xuechuan ^a   Barnes, Charles L ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; CURCUMENE; CURCUPHENOL; PLANT EXTRACT; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEAMINATION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; MICHAEL ADDITION; REDUCTION; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0041379789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01882-3     Document Type: Article

References (38)

1. Harmata M., Hong X. J. Am. Chem. Soc. 125:2003;5754.
2. Bolm C., Hildebrand J.P. Tetrahedron Lett. 37:1998;5731.
3. Bolm C., Hildebrand J.P. J. Org. Chem. 65:2000;169.
4. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
5. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
6. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
7. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
8. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
9. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
10. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
11. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
12. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
13. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
14. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
15. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
16. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
17. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
18. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
19. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
20. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
21. For asymmetric syntheses of curcumene and curcuphenol, see: (a) Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 7, 895; (b) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Chem. Pharm. Bull. 2001, 49, 1581; (c) Kimachi, T.; Takemoto, Y. J. Org. Chem. 2001, 66, 2700; (d) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 3758; (e) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279; (f) Tanaka, K.; Nuruzzaman, M.; Yoshida, M.; Asakawa, N.; Yang, X. ; Tsubaki, K.; Fuji, K. Chem. Pharm. Bull. 1999, 47, 1053; (g) Schmalz, H.; Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620; (h) Sugahara, T.; Ogasawara, K. Tetrahedron: Asymmetry 1998, 9, 2215-2217; (i) Fuganti, C.; Serra, S. Synlett 1998, 1252; (j) Meyers, A. I. ; Stoianova, D. J. Org. Chem. 1997, 62, 5219; (k) Chavan, S. P.; Dhondge, V. J. ; Patil, S. S.; Rao, Y. T. S. Tetrahedron: Asymmetry 1997, 8, 2517; (l) Ono, M. ; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829-1832; (m) Davisson, V. J.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1245; (n) Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc. Commun. 1988, 1538; (o) Asaoka, M.; Shima, K.; Fuji, N.; Takei, H. Tetrahedron 1988, 4757-4766; (p) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 5669; (q) Honda, Y.; Sasaki, M.; Tsuchihashi, G. Chem. Lett. 1985, 1153; (r) Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
22. Simonsen, S. J. The Terpenes; Cambridge University Press, 1952; Vol. III, pp. 18, 202.
23. Honwad V.K., Rao A.S. Tetrahedron. 21:1965;2593.
24. Fusetani N., Sugano M., Matsunaga S., Hashimoto K. Experientia. 43:1987;1234.
25. Wright A.E., Pomponi S.A., McConnell O.J., Kohmoto S., McCarthy P.J. J. Nat. Prod. 50:1987;976.
26. McEnroe F.J., Fenical W. Tetrahedron. 34:1978;1661.
27. Bohlmann F., Lonitz M. Chem. Ber. 111:1978;843.
28. Jolad S.D., Rajagopal S. Org. Synth. 46:1966;13.
29. Crystallographic data (excluding structure factors) for the structures in this paper ( 11 and 12 ), have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 215011 and 215012. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
30. Harmata M., Kahraman M. Synthesis. 1994;142.
31. Johnson T.W., Corey E.J. J. Am. Chem. Soc. 123:2001;4478.
32. 25=+14.6°; Ref. 3n.
33. 25=+42.5°; Ref. 3p.
34. Doyle M.P., Dellaria J.F. Jr., Siegfried B., Bishop S.W. J. Org. Chem. 42:1977;3494.
35. For example, treatment of 4-nitrophenylaniline under the reaction conditions afforded the expected reduction product in 72% yield.
36. 25=-24°; Ref. 3c.
37. 25=+17.8°; Ref. 3i.
38. Boger D.L., Zhou J., Borzilleri R.M., Nukui S., Castle S.L. J. Org. Chem. 62:1997;2054.