A new stereocontrolled entry into the anthracyclinone families. Part 1: Synthesis of bicyclic precursors of 4-demethoxy-7-deoxy-derivatives

Tetrahedron Asymmetry

Volumn 10, Issue 15, 1999, Pages 2935-2944

  García Ruano, José L ^a   Paredes, Cristina García ^a   Hamdouchi, Chafiq ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACYCLINONE DERIVATIVE; BICYCLO COMPOUND;

ARTICLE; CYCLIZATION; ENANTIOMER; PARTIAL DRUG SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0033618519     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00280-3     Document Type: Article

References (52)

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14. For asymmetric synthesis of anthracyclinones see: (a) Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J. J. Chem. Soc., Chem. Commun. 1993, 4, 388; (b) Fujioka, H.; Yamamoto, H.; Annoura, H.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1992, 40, 32; (c) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807; (d) Hauser, F.; Tommasi, R. J. Org. Chem. 1991, 56, 5758; (e) Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867; (f) Tomioka, K.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1989, 1921; (g) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; (h) Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481; (i) Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497; (j) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 3, 367.
15. For asymmetric synthesis of anthracyclinones see: (a) Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J. J. Chem. Soc., Chem. Commun. 1993, 4, 388; (b) Fujioka, H.; Yamamoto, H.; Annoura, H.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1992, 40, 32; (c) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807; (d) Hauser, F.; Tommasi, R. J. Org. Chem. 1991, 56, 5758; (e) Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867; (f) Tomioka, K.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1989, 1921; (g) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; (h) Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481; (i) Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497; (j) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 3, 367.
16. For asymmetric synthesis of anthracyclinones see: (a) Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J. J. Chem. Soc., Chem. Commun. 1993, 4, 388; (b) Fujioka, H.; Yamamoto, H.; Annoura, H.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1992, 40, 32; (c) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807; (d) Hauser, F.; Tommasi, R. J. Org. Chem. 1991, 56, 5758; (e) Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867; (f) Tomioka, K.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1989, 1921; (g) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; (h) Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481; (i) Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497; (j) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 3, 367.
17. For asymmetric synthesis of anthracyclinones see: (a) Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J. J. Chem. Soc., Chem. Commun. 1993, 4, 388; (b) Fujioka, H.; Yamamoto, H.; Annoura, H.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1992, 40, 32; (c) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807; (d) Hauser, F.; Tommasi, R. J. Org. Chem. 1991, 56, 5758; (e) Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867; (f) Tomioka, K.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1989, 1921; (g) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; (h) Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481; (i) Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497; (j) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 3, 367.
18. For asymmetric synthesis of anthracyclinones see: (a) Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J. J. Chem. Soc., Chem. Commun. 1993, 4, 388; (b) Fujioka, H.; Yamamoto, H.; Annoura, H.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1992, 40, 32; (c) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807; (d) Hauser, F.; Tommasi, R. J. Org. Chem. 1991, 56, 5758; (e) Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867; (f) Tomioka, K.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1989, 1921; (g) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; (h) Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481; (i) Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497; (j) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 3, 367.
19. For asymmetric synthesis of anthracyclinones see: (a) Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J. J. Chem. Soc., Chem. Commun. 1993, 4, 388; (b) Fujioka, H.; Yamamoto, H.; Annoura, H.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1992, 40, 32; (c) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807; (d) Hauser, F.; Tommasi, R. J. Org. Chem. 1991, 56, 5758; (e) Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867; (f) Tomioka, K.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1989, 1921; (g) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; (h) Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481; (i) Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497; (j) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 3, 367.
20. For asymmetric synthesis of anthracyclinones see: (a) Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J. J. Chem. Soc., Chem. Commun. 1993, 4, 388; (b) Fujioka, H.; Yamamoto, H.; Annoura, H.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1992, 40, 32; (c) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807; (d) Hauser, F.; Tommasi, R. J. Org. Chem. 1991, 56, 5758; (e) Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867; (f) Tomioka, K.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1989, 1921; (g) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; (h) Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481; (i) Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497; (j) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 3, 367.
21. For asymmetric synthesis of anthracyclinones see: (a) Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J. J. Chem. Soc., Chem. Commun. 1993, 4, 388; (b) Fujioka, H.; Yamamoto, H.; Annoura, H.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1992, 40, 32; (c) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807; (d) Hauser, F.; Tommasi, R. J. Org. Chem. 1991, 56, 5758; (e) Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867; (f) Tomioka, K.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1989, 1921; (g) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; (h) Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481; (i) Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497; (j) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 3, 367.
22. For asymmetric synthesis of anthracyclinones see: (a) Cousson, A.; Le Gouadec, G.; Monneret, C.; Florent, J. J. Chem. Soc., Chem. Commun. 1993, 4, 388; (b) Fujioka, H.; Yamamoto, H.; Annoura, H.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1992, 40, 32; (c) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807; (d) Hauser, F.; Tommasi, R. J. Org. Chem. 1991, 56, 5758; (e) Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867; (f) Tomioka, K.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1989, 1921; (g) Krohn, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 790; (h) Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481; (i) Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497; (j) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 3, 367.
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51. The partial epimerization of hydroxylic centers next to the STol group during desulfenylation has been observed in many cases. See: (a) Butlin, R. J.; Linney, I. D.; Mahon, M. F.; Tye, H.; Wills, M. J. J. Chem. Soc., Perkin Trans. 1 1996, 95; (b) Node, M.; Nishide, K.; Shigeta, Y.; Obata, K.; Shiraki, H.; Kunishige, H. Tetrahedron 1997, 53, 12883.
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