Total synthesis of (-)-lithospermoside

Helvetica Chimica Acta

Volumn 86, Issue 3, 2003, Pages 661-672

  Josien Lefebvre, Delphine ^a   Le Drian, Claude ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

OPTIMIZATION; STERILIZATION (CLEANING); SYNTHESIS (CHEMICAL);

GLYCOSIDATION;

AROMATIC COMPOUNDS;

LITHOSPERMOSIDE; LITHOSPERMUM EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; NONHUMAN; PRIORITY JOURNAL; PRODUCTIVITY; REACTION ANALYSIS; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037254401     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200390065     Document Type: Article

References (45)

1. D. Josien-Lefebvre, C. Le Drian, 'Journées Grand-Est II, Société Française de Chimie', March 29-30, 2001, Nancy, France.
2. a) A. Sosa, C. Sosa-Bourdouil, C. Hardy, C. R. Acad. Sci. 1955, 240, 1570;
3. b) A. Sosa, F. Winternitz, R. Wylde, A. A. Pavia, Phytochemistry 1977, 16, 707.
4. D. Dwuma-Badu, W. H. Watson, E. M. Gopalakrishna, T. U. Okarter, J. E. Knapp, P. L. Schiff, D. J. Slatkin, Lloydia 1976, 39, 385.
5. J. Wu, E. H. Fairchild, J. L. Beal, T. Tomimatsu, R. W. Doskotch, J. Nat. Prod. 1979, 42, 500.
6. a) V. Plouvier, Phytochemistry 1978, 17, 1010;
7. H. Itoh, T. Hatano, M. Miyake, T. Yoshida, M. Kozuka, H. Tokuda, T. Okuda, in 'Polyphenols 94' (Les Colloques, n° 69), INRA Editions, Paris, 1995, p. 419.
8. C. A. Elliger, A. C. Waiss, R. E. Lundin, J. Org. Chem. 1974, 39, 2930; K. Takahashi, S. Matsuzawa, M. Takani, Chem. Pharm. Bull. 1978, 26, 1677; K. Ueda, K. Yasutomi, I. Mori, Chem. Lett. 1983, 149; C. C. Chen, Y. P. Chen, H. Y. Hsu, K. H. Lee, S. Tani, A. T. McPhail, J. Nat. Prod. 1985, 48, 933; A. Nahrstedt, V. Wray, Phytochemistry 1990, 29, 3934; T. P. Abbott, L. K. Nakamura, G. Buchholz, W. J. Wolf, D. M. Palmer, H. J. Gasdorf, T. C. Nelsen, R. Kleiman, J. Agric. Food Chem. 1991, 39, 1488; N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc., Perkin Trans. 1 1992, 1131; T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuno, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang, A. Inada, Chem. Pharm. Bull. 1994, 42, 2251; A. J. J. Van Den Berg, S. F. A. J. Horsten, J. J. Kettenes-Van Den Bosch, B. H. Kroes, R. P. Labadie, Phytochemistry 1995, 40, 597; K. Yamasaki, in 'Advances in Plant Glycosides, Chemistry and Biology', Eds. C.-R. Yang and O. Tanaka, Elsevier, Amsterdam, 1999, p. 335.
9. C. A. Elliger, A. C. Waiss, R. E. Lundin, J. Org. Chem. 1974, 39, 2930; K. Takahashi, S. Matsuzawa, M. Takani, Chem. Pharm. Bull. 1978, 26, 1677; K. Ueda, K. Yasutomi, I. Mori, Chem. Lett. 1983, 149; C. C. Chen, Y. P. Chen, H. Y. Hsu, K. H. Lee, S. Tani, A. T. McPhail, J. Nat. Prod. 1985, 48, 933; A. Nahrstedt, V. Wray, Phytochemistry 1990, 29, 3934; T. P. Abbott, L. K. Nakamura, G. Buchholz, W. J. Wolf, D. M. Palmer, H. J. Gasdorf, T. C. Nelsen, R. Kleiman, J. Agric. Food Chem. 1991, 39, 1488; N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc., Perkin Trans. 1 1992, 1131; T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuno, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang, A. Inada, Chem. Pharm. Bull. 1994, 42, 2251; A. J. J. Van Den Berg, S. F. A. J. Horsten, J. J. Kettenes-Van Den Bosch, B. H. Kroes, R. P. Labadie, Phytochemistry 1995, 40, 597; K. Yamasaki, in 'Advances in Plant Glycosides, Chemistry and Biology', Eds. C.-R. Yang and O. Tanaka, Elsevier, Amsterdam, 1999, p. 335.
10. C. A. Elliger, A. C. Waiss, R. E. Lundin, J. Org. Chem. 1974, 39, 2930; K. Takahashi, S. Matsuzawa, M. Takani, Chem. Pharm. Bull. 1978, 26, 1677; K. Ueda, K. Yasutomi, I. Mori, Chem. Lett. 1983, 149; C. C. Chen, Y. P. Chen, H. Y. Hsu, K. H. Lee, S. Tani, A. T. McPhail, J. Nat. Prod. 1985, 48, 933; A. Nahrstedt, V. Wray, Phytochemistry 1990, 29, 3934; T. P. Abbott, L. K. Nakamura, G. Buchholz, W. J. Wolf, D. M. Palmer, H. J. Gasdorf, T. C. Nelsen, R. Kleiman, J. Agric. Food Chem. 1991, 39, 1488; N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc., Perkin Trans. 1 1992, 1131; T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuno, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang, A. Inada, Chem. Pharm. Bull. 1994, 42, 2251; A. J. J. Van Den Berg, S. F. A. J. Horsten, J. J. Kettenes-Van Den Bosch, B. H. Kroes, R. P. Labadie, Phytochemistry 1995, 40, 597; K. Yamasaki, in 'Advances in Plant Glycosides, Chemistry and Biology', Eds. C.-R. Yang and O. Tanaka, Elsevier, Amsterdam, 1999, p. 335.
11. C. A. Elliger, A. C. Waiss, R. E. Lundin, J. Org. Chem. 1974, 39, 2930; K. Takahashi, S. Matsuzawa, M. Takani, Chem. Pharm. Bull. 1978, 26, 1677; K. Ueda, K. Yasutomi, I. Mori, Chem. Lett. 1983, 149; C. C. Chen, Y. P. Chen, H. Y. Hsu, K. H. Lee, S. Tani, A. T. McPhail, J. Nat. Prod. 1985, 48, 933; A. Nahrstedt, V. Wray, Phytochemistry 1990, 29, 3934; T. P. Abbott, L. K. Nakamura, G. Buchholz, W. J. Wolf, D. M. Palmer, H. J. Gasdorf, T. C. Nelsen, R. Kleiman, J. Agric. Food Chem. 1991, 39, 1488; N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc., Perkin Trans. 1 1992, 1131; T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuno, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang, A. Inada, Chem. Pharm. Bull. 1994, 42, 2251; A. J. J. Van Den Berg, S. F. A. J. Horsten, J. J. Kettenes-Van Den Bosch, B. H. Kroes, R. P. Labadie, Phytochemistry 1995, 40, 597; K. Yamasaki, in 'Advances in Plant Glycosides, Chemistry and Biology', Eds. C.-R. Yang and O. Tanaka, Elsevier, Amsterdam, 1999, p. 335.
12. C. A. Elliger, A. C. Waiss, R. E. Lundin, J. Org. Chem. 1974, 39, 2930; K. Takahashi, S. Matsuzawa, M. Takani, Chem. Pharm. Bull. 1978, 26, 1677; K. Ueda, K. Yasutomi, I. Mori, Chem. Lett. 1983, 149; C. C. Chen, Y. P. Chen, H. Y. Hsu, K. H. Lee, S. Tani, A. T. McPhail, J. Nat. Prod. 1985, 48, 933; A. Nahrstedt, V. Wray, Phytochemistry 1990, 29, 3934; T. P. Abbott, L. K. Nakamura, G. Buchholz, W. J. Wolf, D. M. Palmer, H. J. Gasdorf, T. C. Nelsen, R. Kleiman, J. Agric. Food Chem. 1991, 39, 1488; N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc., Perkin Trans. 1 1992, 1131; T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuno, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang, A. Inada, Chem. Pharm. Bull. 1994, 42, 2251; A. J. J. Van Den Berg, S. F. A. J. Horsten, J. J. Kettenes-Van Den Bosch, B. H. Kroes, R. P. Labadie, Phytochemistry 1995, 40, 597; K. Yamasaki, in 'Advances in Plant Glycosides, Chemistry and Biology', Eds. C.-R. Yang and O. Tanaka, Elsevier, Amsterdam, 1999, p. 335.
13. C. A. Elliger, A. C. Waiss, R. E. Lundin, J. Org. Chem. 1974, 39, 2930; K. Takahashi, S. Matsuzawa, M. Takani, Chem. Pharm. Bull. 1978, 26, 1677; K. Ueda, K. Yasutomi, I. Mori, Chem. Lett. 1983, 149; C. C. Chen, Y. P. Chen, H. Y. Hsu, K. H. Lee, S. Tani, A. T. McPhail, J. Nat. Prod. 1985, 48, 933; A. Nahrstedt, V. Wray, Phytochemistry 1990, 29, 3934; T. P. Abbott, L. K. Nakamura, G. Buchholz, W. J. Wolf, D. M. Palmer, H. J. Gasdorf, T. C. Nelsen, R. Kleiman, J. Agric. Food Chem. 1991, 39, 1488; N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc., Perkin Trans. 1 1992, 1131; T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuno, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang, A. Inada, Chem. Pharm. Bull. 1994, 42, 2251; A. J. J. Van Den Berg, S. F. A. J. Horsten, J. J. Kettenes-Van Den Bosch, B. H. Kroes, R. P. Labadie, Phytochemistry 1995, 40, 597; K. Yamasaki, in 'Advances in Plant Glycosides, Chemistry and Biology', Eds. C.-R. Yang and O. Tanaka, Elsevier, Amsterdam, 1999, p. 335.
14. C. A. Elliger, A. C. Waiss, R. E. Lundin, J. Org. Chem. 1974, 39, 2930; K. Takahashi, S. Matsuzawa, M. Takani, Chem. Pharm. Bull. 1978, 26, 1677; K. Ueda, K. Yasutomi, I. Mori, Chem. Lett. 1983, 149; C. C. Chen, Y. P. Chen, H. Y. Hsu, K. H. Lee, S. Tani, A. T. McPhail, J. Nat. Prod. 1985, 48, 933; A. Nahrstedt, V. Wray, Phytochemistry 1990, 29, 3934; T. P. Abbott, L. K. Nakamura, G. Buchholz, W. J. Wolf, D. M. Palmer, H. J. Gasdorf, T. C. Nelsen, R. Kleiman, J. Agric. Food Chem. 1991, 39, 1488; N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc., Perkin Trans. 1 1992, 1131; T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuno, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang, A. Inada, Chem. Pharm. Bull. 1994, 42, 2251; A. J. J. Van Den Berg, S. F. A. J. Horsten, J. J. Kettenes-Van Den Bosch, B. H. Kroes, R. P. Labadie, Phytochemistry 1995, 40, 597; K. Yamasaki, in 'Advances in Plant Glycosides, Chemistry and Biology', Eds. C.-R. Yang and O. Tanaka, Elsevier, Amsterdam, 1999, p. 335.
15. C. A. Elliger, A. C. Waiss, R. E. Lundin, J. Org. Chem. 1974, 39, 2930; K. Takahashi, S. Matsuzawa, M. Takani, Chem. Pharm. Bull. 1978, 26, 1677; K. Ueda, K. Yasutomi, I. Mori, Chem. Lett. 1983, 149; C. C. Chen, Y. P. Chen, H. Y. Hsu, K. H. Lee, S. Tani, A. T. McPhail, J. Nat. Prod. 1985, 48, 933; A. Nahrstedt, V. Wray, Phytochemistry 1990, 29, 3934; T. P. Abbott, L. K. Nakamura, G. Buchholz, W. J. Wolf, D. M. Palmer, H. J. Gasdorf, T. C. Nelsen, R. Kleiman, J. Agric. Food Chem. 1991, 39, 1488; N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc., Perkin Trans. 1 1992, 1131; T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuno, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang, A. Inada, Chem. Pharm. Bull. 1994, 42, 2251; A. J. J. Van Den Berg, S. F. A. J. Horsten, J. J. Kettenes-Van Den Bosch, B. H. Kroes, R. P. Labadie, Phytochemistry 1995, 40, 597; K. Yamasaki, in 'Advances in Plant Glycosides, Chemistry and Biology', Eds. C.-R. Yang and O. Tanaka, Elsevier, Amsterdam, 1999, p. 335.
16. C. A. Elliger, A. C. Waiss, R. E. Lundin, J. Org. Chem. 1974, 39, 2930; K. Takahashi, S. Matsuzawa, M. Takani, Chem. Pharm. Bull. 1978, 26, 1677; K. Ueda, K. Yasutomi, I. Mori, Chem. Lett. 1983, 149; C. C. Chen, Y. P. Chen, H. Y. Hsu, K. H. Lee, S. Tani, A. T. McPhail, J. Nat. Prod. 1985, 48, 933; A. Nahrstedt, V. Wray, Phytochemistry 1990, 29, 3934; T. P. Abbott, L. K. Nakamura, G. Buchholz, W. J. Wolf, D. M. Palmer, H. J. Gasdorf, T. C. Nelsen, R. Kleiman, J. Agric. Food Chem. 1991, 39, 1488; N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc., Perkin Trans. 1 1992, 1131; T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuno, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang, A. Inada, Chem. Pharm. Bull. 1994, 42, 2251; A. J. J. Van Den Berg, S. F. A. J. Horsten, J. J. Kettenes-Van Den Bosch, B. H. Kroes, R. P. Labadie, Phytochemistry 1995, 40, 597; K. Yamasaki, in 'Advances in Plant Glycosides, Chemistry and Biology', Eds. C.-R. Yang and O. Tanaka, Elsevier, Amsterdam, 1999, p. 335.
17. C. A. Elliger, A. C. Waiss, R. E. Lundin, J. Org. Chem. 1974, 39, 2930; K. Takahashi, S. Matsuzawa, M. Takani, Chem. Pharm. Bull. 1978, 26, 1677; K. Ueda, K. Yasutomi, I. Mori, Chem. Lett. 1983, 149; C. C. Chen, Y. P. Chen, H. Y. Hsu, K. H. Lee, S. Tani, A. T. McPhail, J. Nat. Prod. 1985, 48, 933; A. Nahrstedt, V. Wray, Phytochemistry 1990, 29, 3934; T. P. Abbott, L. K. Nakamura, G. Buchholz, W. J. Wolf, D. M. Palmer, H. J. Gasdorf, T. C. Nelsen, R. Kleiman, J. Agric. Food Chem. 1991, 39, 1488; N. Chida, K. Yamada, S. Ogawa, J. Chem. Soc., Perkin Trans. 1 1992, 1131; T. Nakanishi, M. Nishi, M. Somekawa, H. Murata, M. Mizuno, M. Iinuma, T. Tanaka, J. Murata, F. A. Lang, A. Inada, Chem. Pharm. Bull. 1994, 42, 2251; A. J. J. Van Den Berg, S. F. A. J. Horsten, J. J. Kettenes-Van Den Bosch, B. H. Kroes, R. P. Labadie, Phytochemistry 1995, 40, 597; K. Yamasaki, in 'Advances in Plant Glycosides, Chemistry and Biology', Eds. C.-R. Yang and O. Tanaka, Elsevier, Amsterdam, 1999, p. 335.
18. D. Josien-Lefebvre, G. Desmares, C. Le Drian, Helv. Chim. Acta 2001, 84, 890.
19. E. Vieira, P. Vogel, Helv. Chim. Acta 1983, 66, 1865; K. A. Black, P. Vogel, Helv. Chim. Acta 1984, 67, 1612; A. Warm, P. Vogel, J. Org. Chem. 1986, 51, 5348; J. L. Reymond, P. Vogel, Tetrahedron: Asymmetry 1990, 1, 729; A. Forster, T. Kovac, H. Mosimann, P. Renaud, P. Vogel, Tetrahedron: Asymmetry 1999, 10, 567.
20. E. Vieira, P. Vogel, Helv. Chim. Acta 1983, 66, 1865; K. A. Black, P. Vogel, Helv. Chim. Acta 1984, 67, 1612; A. Warm, P. Vogel, J. Org. Chem. 1986, 51, 5348; J. L. Reymond, P. Vogel, Tetrahedron: Asymmetry 1990, 1, 729; A. Forster, T. Kovac, H. Mosimann, P. Renaud, P. Vogel, Tetrahedron: Asymmetry 1999, 10, 567.
21. E. Vieira, P. Vogel, Helv. Chim. Acta 1983, 66, 1865; K. A. Black, P. Vogel, Helv. Chim. Acta 1984, 67, 1612; A. Warm, P. Vogel, J. Org. Chem. 1986, 51, 5348; J. L. Reymond, P. Vogel, Tetrahedron: Asymmetry 1990, 1, 729; A. Forster, T. Kovac, H. Mosimann, P. Renaud, P. Vogel, Tetrahedron: Asymmetry 1999, 10, 567.
22. E. Vieira, P. Vogel, Helv. Chim. Acta 1983, 66, 1865; K. A. Black, P. Vogel, Helv. Chim. Acta 1984, 67, 1612; A. Warm, P. Vogel, J. Org. Chem. 1986, 51, 5348; J. L. Reymond, P. Vogel, Tetrahedron: Asymmetry 1990, 1, 729; A. Forster, T. Kovac, H. Mosimann, P. Renaud, P. Vogel, Tetrahedron: Asymmetry 1999, 10, 567.
23. E. Vieira, P. Vogel, Helv. Chim. Acta 1983, 66, 1865; K. A. Black, P. Vogel, Helv. Chim. Acta 1984, 67, 1612; A. Warm, P. Vogel, J. Org. Chem. 1986, 51, 5348; J. L. Reymond, P. Vogel, Tetrahedron: Asymmetry 1990, 1, 729; A. Forster, T. Kovac, H. Mosimann, P. Renaud, P. Vogel, Tetrahedron: Asymmetry 1999, 10, 567.
24. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
25. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
26. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
27. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
28. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
29. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
30. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
31. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
32. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
33. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
34. a) C. Le Drian, E. Vieira, P. Vogel, Helv. Chim. Acta 1989, 72, 338; P. Vogel, D. Fattori, F. Gasparini, C. Le Drian, Synlett 1990, 4, 173; S. Jeganathan, P. Vogel, Tetrahedron Lett. 1990, 31, 1717; E. de Guchteneere, D. Fattori, P. Vogel, Tetrahedron 1992, 48, 10603; O. Arjona, A. de Dios, J. Plumet, B. Saez, Tetrahedron Lett. 1995, 36, 1319; O. Arjona, A. de Dios, J. Plumet, B. Saez, J. Org. Chem. 1995, 60, 4932; J. Cossy, J.-L. Ranaivosata, V. Bellosta, Tetrahedron 1996, 52, 629; N. Jotterand, P. Vogel, Synlett 1998, 1237; P. Renaut, J. Millet, C. Sepulchre, J. Theveniaux, V. Barberousse, V. Jeanneret, P. Vogel, Helv. Chim. Acta 1998, 81, 2043; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 3485; A. Forster, J. Fitremann, P. Renaud, Tetrahedron Lett. 1998, 39, 7097;
35. b) C. Le Drian, J. P. Vionnet, P. Vogel, Helv. Chim. Acta 1990, 73, 161.
36. G. Desmares, D. Lefebvre, G. Renevret, C. Le Drian, Helv. Chim. Acta 2001, 84, 880.
37. C. Le Drian, P. Vogel, Helv. Chim. Acta 1987, 70, 1703.
38. a) K.-H. Chung, H. G. Lee, I.-Y. Choi, J.-R. Choi, J. Org. Chem. 2001, 66, 5937;
39. b) D. B. Berkowitz, S. Choi, J.-H. Maeng, J. Org. Chem. 2000, 56, 847;
40. c) M. Kawanisi, Y. Itoh, T. Hieda, S. Kozima, T. Hitomi, K. Kobayashi, Chem. Lett. 1985, 647; R. Cacciapaglia, L. Mandolini, J. Org. Chem. 1988, 63, 2579.
41. c) M. Kawanisi, Y. Itoh, T. Hieda, S. Kozima, T. Hitomi, K. Kobayashi, Chem. Lett. 1985, 647; R. Cacciapaglia, L. Mandolini, J. Org. Chem. 1988, 63, 2579.
42. K. Fuji, S. Nakano, E. Fujita, Synthesis 1975, 276.
43. S. Sugiyama, M. Honda, R. Higuchi, T. Komori, Liebigs Ann. Chem. 1991, 349; D. R. Kelly, S. M. Roberts, R. F. Newton, Synth. Commun. 1979, 9, 295.
44. S. Sugiyama, M. Honda, R. Higuchi, T. Komori, Liebigs Ann. Chem. 1991, 349; D. R. Kelly, S. M. Roberts, R. F. Newton, Synth. Commun. 1979, 9, 295.
45. D. D. Perrin, W. L. F. Armarego, 'Purification of Laboratory Chemicals', 3rd edn., Pergamon Press, Oxford, 1988.