Remote control of dieis-alder additions. Enantioselective synthesis of (2r). 1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural

Tetrahedron Asymmetry

Volumn 8, Issue 20, 1997, Pages 3497-3501

  Theurillat Moritz, Viviane ^b   Guidi, Antonio ^a,b   Vogel, Pierre ^b  

^a BCH ^*  (Italy)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACYCLINE; FURFURAL; KETONE DERIVATIVE; NORBORNENE DERIVATIVE;

ARTICLE; ENANTIOMER; PRIORITY JOURNAL; PURIFICATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030702064     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00433-3     Document Type: Article

References (34)

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2. Métral, J.-L.; Lauterwein, J.; Vogel, P. Helv. Chim. Acta 1986, 69, 1287-1309.
3. Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729-736.
4. Dienes, Z.; Vogel, P. J. Org. Chem. 1996, 61, 6958-6970.
5. Guidi, A.; Theurillat-Moritz, V.; Vogel, P.; Pinkerton, A. A. Tetrahedron: Asymmetry 1996, 7, 3153-3162.
6. Wong, C. M.; Popien, D.; Schwenk, R.; Te Raa, J. Can. J. Chem. 1971, 49, 2712-2718.
7. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
8. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
9. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
10. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
11. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
12. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
13. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
14. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
15. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
16. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
17. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
18. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
19. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
20. Arcamone, F.; Bernardi, L.; Patelli, B.; Giardino, P.; Di Marco, A.; Casazza, A. M.; Soranzo, C.; Pratesi, G. Experientia 1978, 34, 1255-1257; Broadhurst, M. J.; Hassall, C. H.; Thomas, G. J. J. Chem. Soc., Perkin Trans. I 1982, 2239-2248, 2249-2255; Swenton, J. S.; Freskos, J. N.; Morrow, G. W.; Sercel, A. D. Tetrahedron 1984, 40, 4625-4632; Terashima, S.; Jew, S.-S.; Koga, K. Tetrahedron Lett. 1978, 19, 4937-4940; Terashima, S.; Tamoto, K. Ibid. 1982, 23, 3715-3718; Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1985, 367-370; Suzuki, M.; Kimura, Y.; Terashima, S. Tetrahedron Lett. 1985, 26, 6481-6484; Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559-3572; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Comm. 1991, 1533-1534; Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867-870; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. J. Chem. Soc., Chem. Comm. 1984, 453-455; Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643-4647; Sodeoka, M.; Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 6497-6500; Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 10807-10816.
21. Arcamone, F. M.; Bernardi, L.; Patelli, B.; Di Marco, A.; Ger Offen 2601785, Chem. Abstr. 1976 85: P 142918 j.
22. See e.g.: Lown, L. W. Chem. Soc. Rev. 1993, 165-176; Priebe, W. Anthracycline Antibiotics: New Analogues, Methodes of Delivery and Mechanisms of Action; ACS Symposium Series 574; American Chemical Society: Washington, D.C., 1995; Weiss, R. B. Semin. Oncol. 1992, 19, 670-686.
23. See e.g.: Lown, L. W. Chem. Soc. Rev. 1993, 165-176; Priebe, W. Anthracycline Antibiotics: New Analogues, Methodes of Delivery and Mechanisms of Action; ACS Symposium Series 574; American Chemical Society: Washington, D.C., 1995; Weiss, R. B. Semin. Oncol. 1992, 19, 670-686.
24. See e.g.: Lown, L. W. Chem. Soc. Rev. 1993, 165-176; Priebe, W. Anthracycline Antibiotics: New Analogues, Methodes of Delivery and Mechanisms of Action; ACS Symposium Series 574; American Chemical Society: Washington, D.C., 1995; Weiss, R. B. Semin. Oncol. 1992, 19, 670-686.
25. Hardy, M.; Carrupt, P.-A.; Vogel, P. Helv. Chim. Acta 1976, 59, 1685-1697; Carrupt, P.-A.; Vogel, P. Tetrahedron Lett. 1979, 4533-4536; Vogel, P. in Advances in Theoretically Interesting Molecules, Ed. R. P. Thummel, JAI Press, Inc., Greewich, CT, USA, 1989, vol. 1, p. 201-355; Roulet, J.-M.; Vogel, P.; Wiesemann, F.; Pinkerton, A. A. Tetrahedron 1995, 51, 1685-1696.
26. Hardy, M.; Carrupt, P.-A.; Vogel, P. Helv. Chim. Acta 1976, 59, 1685-1697; Carrupt, P.-A.; Vogel, P. Tetrahedron Lett. 1979, 4533-4536; Vogel, P. in Advances in Theoretically Interesting Molecules, Ed. R. P. Thummel, JAI Press, Inc., Greewich, CT, USA, 1989, vol. 1, p. 201-355; Roulet, J.-M.; Vogel, P.; Wiesemann, F.; Pinkerton, A. A. Tetrahedron 1995, 51, 1685-1696.
27. Hardy, M.; Carrupt, P.-A.; Vogel, P. Helv. Chim. Acta 1976, 59, 1685-1697; Carrupt, P.-A.; Vogel, P. Tetrahedron Lett. 1979, 4533-4536; Vogel, P. in Advances in Theoretically Interesting Molecules, Ed. R. P. Thummel, JAI Press, Inc., Greewich, CT, USA, 1989, vol. 1, p. 201-355; Roulet, J.-M.; Vogel, P.; Wiesemann, F.; Pinkerton, A. A. Tetrahedron 1995, 51, 1685-1696.
28. Hardy, M.; Carrupt, P.-A.; Vogel, P. Helv. Chim. Acta 1976, 59, 1685-1697; Carrupt, P.-A.; Vogel, P. Tetrahedron Lett. 1979, 4533-4536; Vogel, P. in Advances in Theoretically Interesting Molecules, Ed. R. P. Thummel, JAI Press, Inc., Greewich, CT, USA, 1989, vol. 1, p. 201-355; Roulet, J.-M.; Vogel, P.; Wiesemann, F.; Pinkerton, A. A. Tetrahedron 1995, 51, 1685-1696.
29. Tamariz, J.; Vogel, P. Helv. Chim. Acta 1981, 64, 188-197.
30. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
31. Terashima, S.; Tamoto, K. Tetrahedron Lett. 1983, 24, 2589-2592.
32. Stothers, J. B. in Carbon-13 NMR Spectroscopy, Academic Press, New York, 1972; Olah, G. A.; Schlosberg, R. H.; Kelly, D. P.; Mateescu, G. D. J. Am. Chem. Soc. 1970, 92, 2546-2548.
33. Stothers, J. B. in Carbon-13 NMR Spectroscopy, Academic Press, New York, 1972; Olah, G. A.; Schlosberg, R. H.; Kelly, D. P.; Mateescu, G. D. J. Am. Chem. Soc. 1970, 92, 2546-2548.
34. Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077-2092.