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Volumn 79, Issue 5, 1996, Pages 1393-1414

117. A new approach to the synthesis of long-chain polypropionates based on the Diels-Alder monoadditions of 2,2′-ethylidenebis[3,5-dimethylfuran]

(2) Ancerewicz, Jacek a Vogel, Pierre a

a UNIVERSITY OF LAUSANNE (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

PROPIONIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; POLYMERIZATION; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030038617 PISSN: 0018019X EISSN: None Source Type: Journal
DOI: 10.1002/hlca.19960790513 Document Type: Article

Times cited : (28)

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49
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- See eg.: a) methymycine: S. Masamune, C. U. Kim, K. E. Wilson, G. O. Spessard, P. E. Georghiou, G. S. Bates, J. Am. Chem. Soc. 1975, 97, 3512; R. E. Ireland, J. P. Daub, J. Org. Chem. 1983, 48, 1303; R. E. Ireland, J P. Daub, G. S. Mandel, N. S. Mandel, ibid. 1983, 48, 1312; P. A. Grieco, Y. Ohfune, Y. Yokoyama, W. Owens, J. Am. Chem. Soc. 1979, 101, 4749;
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 4749
- Grieco, P.A.¹ Ohfune, Y.² Yokoyama, Y.³ Owens, W.⁴

50
- 0022493303
- b) pikromycin: N. Nakajima, T. Hamada, T. Tanaka, Y. Oikawa, O. Yonemitsu, ibid. 1986, 108, 4645;
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 4645
- Nakajima, N.¹ Hamada, T.² Tanaka, T.³ Oikawa, Y.⁴ Yonemitsu, O.⁵

51
- 0342393226
- c) erythromycin: S. Hanessian, G. Rancourt, Y. Guindon, Can. J. Chem. 1978, 56, 1843; G. Stork, S. D. Rychnovsky, J. Am. Chem. Soc. 1987, 109, 1565; H Tone, T. Nishi, Y. Oikawa, M. Hikota, O. Yonemitsu, Tetrahedron Lett. 1987, 28, 4569; J. Mulzer, H. M. Kirstein, J. Buschmann, C. Lehmann, P. Luger. J. Am. Chem. Soc. 1991, 113, 910; J. Mulzer, H. Kirstein, P. Mareski, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 111; R W. Hoffmann, R. Stürmer, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 103; R Stürmer, K. Ritter, R. W. Hoffmann, Angew Chem. Int. Ed. 1993, 32, 101; R. Stürmer, R. W. Hoffmann, Chem. Ber. 1994, 127, 2519,
- (1978) Can. J. Chem. , vol.56 , pp. 1843
- Hanessian, S.¹ Rancourt, G.² Guindon, Y.³

52
- 0023153093
- c) erythromycin: S. Hanessian, G. Rancourt, Y. Guindon, Can. J. Chem. 1978, 56, 1843; G. Stork, S. D. Rychnovsky, J. Am. Chem. Soc. 1987, 109, 1565; H Tone, T. Nishi, Y. Oikawa, M. Hikota, O. Yonemitsu, Tetrahedron Lett. 1987, 28, 4569; J. Mulzer, H. M. Kirstein, J. Buschmann, C. Lehmann, P. Luger. J. Am. Chem. Soc. 1991, 113, 910; J. Mulzer, H. Kirstein, P. Mareski, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 111; R W. Hoffmann, R. Stürmer, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 103; R Stürmer, K. Ritter, R. W. Hoffmann, Angew Chem. Int. Ed. 1993, 32, 101; R. Stürmer, R. W. Hoffmann, Chem. Ber. 1994, 127, 2519,
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 1565
- Stork, G.¹ Rychnovsky, S.D.²

53
- 0023259304
- c) erythromycin: S. Hanessian, G. Rancourt, Y. Guindon, Can. J. Chem. 1978, 56, 1843; G. Stork, S. D. Rychnovsky, J. Am. Chem. Soc. 1987, 109, 1565; H Tone, T. Nishi, Y. Oikawa, M. Hikota, O. Yonemitsu, Tetrahedron Lett. 1987, 28, 4569; J. Mulzer, H. M. Kirstein, J. Buschmann, C. Lehmann, P. Luger. J. Am. Chem. Soc. 1991, 113, 910; J. Mulzer, H. Kirstein, P. Mareski, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 111; R W. Hoffmann, R. Stürmer, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 103; R Stürmer, K. Ritter, R. W. Hoffmann, Angew Chem. Int. Ed. 1993, 32, 101; R. Stürmer, R. W. Hoffmann, Chem. Ber. 1994, 127, 2519,
- (1987) Tetrahedron Lett. , vol.28 , pp. 4569
- Tone, H.¹ Nishi, T.² Oikawa, Y.³ Hikota, M.⁴ Yonemitsu, O.⁵

54
- 0026097004
- c) erythromycin: S. Hanessian, G. Rancourt, Y. Guindon, Can. J. Chem. 1978, 56, 1843; G. Stork, S. D. Rychnovsky, J. Am. Chem. Soc. 1987, 109, 1565; H Tone, T. Nishi, Y. Oikawa, M. Hikota, O. Yonemitsu, Tetrahedron Lett. 1987, 28, 4569; J. Mulzer, H. M. Kirstein, J. Buschmann, C. Lehmann, P. Luger. J. Am. Chem. Soc. 1991, 113, 910; J. Mulzer, H. Kirstein, P. Mareski, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 111; R W. Hoffmann, R. Stürmer, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 103; R Stürmer, K. Ritter, R. W. Hoffmann, Angew Chem. Int. Ed. 1993, 32, 101; R. Stürmer, R. W. Hoffmann, Chem. Ber. 1994, 127, 2519,
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 910
- Mulzer, J.¹ Kirstein, H.M.² Buschmann, J.³ Lehmann, C.⁴ Luger, P.⁵

55
- 0003853085
- VCH, Weinheim
- c) erythromycin: S. Hanessian, G. Rancourt, Y. Guindon, Can. J. Chem. 1978, 56, 1843; G. Stork, S. D. Rychnovsky, J. Am. Chem. Soc. 1987, 109, 1565; H Tone, T. Nishi, Y. Oikawa, M. Hikota, O. Yonemitsu, Tetrahedron Lett. 1987, 28, 4569; J. Mulzer, H. M. Kirstein, J. Buschmann, C. Lehmann, P. Luger. J. Am. Chem. Soc. 1991, 113, 910; J. Mulzer, H. Kirstein, P. Mareski, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 111; R W. Hoffmann, R. Stürmer, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 103; R Stürmer, K. Ritter, R. W. Hoffmann, Angew Chem. Int. Ed. 1993, 32, 101; R. Stürmer, R. W. Hoffmann, Chem. Ber. 1994, 127, 2519,
- (1993) Antibiotics and Antiviral Compounds , pp. 111
- Mulzer, J.¹ Kirstein, H.² Mareski, P.³

56
- 0003853085
- VCH, Weinheim
- c) erythromycin: S. Hanessian, G. Rancourt, Y. Guindon, Can. J. Chem. 1978, 56, 1843; G. Stork, S. D. Rychnovsky, J. Am. Chem. Soc. 1987, 109, 1565; H Tone, T. Nishi, Y. Oikawa, M. Hikota, O. Yonemitsu, Tetrahedron Lett. 1987, 28, 4569; J. Mulzer, H. M. Kirstein, J. Buschmann, C. Lehmann, P. Luger. J. Am. Chem. Soc. 1991, 113, 910; J. Mulzer, H. Kirstein, P. Mareski, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 111; R W. Hoffmann, R. Stürmer, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 103; R Stürmer, K. Ritter, R. W. Hoffmann, Angew Chem. Int. Ed. 1993, 32, 101; R. Stürmer, R. W. Hoffmann, Chem. Ber. 1994, 127, 2519,
- (1993) Antibiotics and Antiviral Compounds , pp. 103
- Hoffmann, R.W.¹ Stürmer, R.²

57
- 33748244238
- c) erythromycin: S. Hanessian, G. Rancourt, Y. Guindon, Can. J. Chem. 1978, 56, 1843; G. Stork, S. D. Rychnovsky, J. Am. Chem. Soc. 1987, 109, 1565; H Tone, T. Nishi, Y. Oikawa, M. Hikota, O. Yonemitsu, Tetrahedron Lett. 1987, 28, 4569; J. Mulzer, H. M. Kirstein, J. Buschmann, C. Lehmann, P. Luger. J. Am. Chem. Soc. 1991, 113, 910; J. Mulzer, H. Kirstein, P. Mareski, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 111; R W. Hoffmann, R. Stürmer, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 103; R Stürmer, K. Ritter, R. W. Hoffmann, Angew Chem. Int. Ed. 1993, 32, 101; R. Stürmer, R. W. Hoffmann, Chem. Ber. 1994, 127, 2519,
- (1993) Angew Chem. Int. Ed. , vol.32 , pp. 101
- Stürmer, R.¹ Ritter, K.² Hoffmann, R.W.³

58
- 84989457089
- c) erythromycin: S. Hanessian, G. Rancourt, Y. Guindon, Can. J. Chem. 1978, 56, 1843; G. Stork, S. D. Rychnovsky, J. Am. Chem. Soc. 1987, 109, 1565; H Tone, T. Nishi, Y. Oikawa, M. Hikota, O. Yonemitsu, Tetrahedron Lett. 1987, 28, 4569; J. Mulzer, H. M. Kirstein, J. Buschmann, C. Lehmann, P. Luger. J. Am. Chem. Soc. 1991, 113, 910; J. Mulzer, H. Kirstein, P. Mareski, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 111; R W. Hoffmann, R. Stürmer, in 'Antibiotics and Antiviral Compounds', VCH, Weinheim, 1993, p. 103; R Stürmer, K. Ritter, R. W. Hoffmann, Angew Chem. Int. Ed. 1993, 32, 101; R. Stürmer, R. W. Hoffmann, Chem. Ber. 1994, 127, 2519,
- (1994) Chem. Ber. , vol.127 , pp. 2519
- Stürmer, R.¹ Hoffmann, R.W.²

59
- 0025190026
- d) oleandomycin. K. Tatsuta, T. Ishiyama, S. Tajima, Y. Koguchi, H. Gunji, Tetrahedron Lett. 1990, 31, 709; I. Paterson, R A. Ward, P. Romea, R D. Norcross, J. Am. Chem. Soc. 1994, 116, 3623; I. Paterson. R. D. Norcross, R. A. Ward, P. Romea, M. A. Lister, ibid. 1994, 116, 11287;
- (1990) Tetrahedron Lett. , vol.31 , pp. 709
- Tatsuta, K.¹ Ishiyama, T.² Tajima, S.³ Koguchi, Y.⁴ Gunji, H.⁵

60
- 0028228096
- d) oleandomycin. K. Tatsuta, T. Ishiyama, S. Tajima, Y. Koguchi, H. Gunji, Tetrahedron Lett. 1990, 31, 709; I. Paterson, R A. Ward, P. Romea, R D. Norcross, J. Am. Chem. Soc. 1994, 116, 3623; I. Paterson. R. D. Norcross, R. A. Ward, P. Romea, M. A. Lister, ibid. 1994, 116, 11287;
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 3623
- Paterson, I.¹ Ward, R.A.² Romea, P.³ Norcross, R.D.⁴

61
- 0028604352
- d) oleandomycin. K. Tatsuta, T. Ishiyama, S. Tajima, Y. Koguchi, H. Gunji, Tetrahedron Lett. 1990, 31, 709; I. Paterson, R A. Ward, P. Romea, R D. Norcross, J. Am. Chem. Soc. 1994, 116, 3623; I. Paterson. R. D. Norcross, R. A. Ward, P. Romea, M. A. Lister, ibid. 1994, 116, 11287;
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 11287
- Paterson, I.¹ Norcross, R.D.² Ward, R.A.³ Romea, P.⁴ Lister, M.A.⁵

62
- 0040992120
- e) carbomycin: K. C. Nicolaou, M. R. Pavia, S P. Seitz, Tetrahedron Lett. 1979, 2327; K. Tatsuta, Y. Amemiya, S. Maniwa, M. Kinoshita, ibid. 1980, 21, 2837; K C. Nicolaou, S. P. Seitz, M. R. Pavia, J. Am. Chem. Soc. 1981, 103, 1222; K. C. Nicolaou, M. R. Pavia, S. P. Seitz, ibid. 1981, 103, 1224;
- (1979) Tetrahedron Lett. , pp. 2327
- Nicolaou, K.C.¹ Pavia, M.R.² Seitz, S.P.³

63
- 0010634340
- e) carbomycin: K. C. Nicolaou, M. R. Pavia, S P. Seitz, Tetrahedron Lett. 1979, 2327; K. Tatsuta, Y. Amemiya, S. Maniwa, M. Kinoshita, ibid. 1980, 21, 2837; K C. Nicolaou, S. P. Seitz, M. R. Pavia, J. Am. Chem. Soc. 1981, 103, 1222; K. C. Nicolaou, M. R. Pavia, S. P. Seitz, ibid. 1981, 103, 1224;
- (1980) Tetrahedron Lett. , vol.21 , pp. 2837
- Tatsuta, K.¹ Amemiya, Y.² Maniwa, S.³ Kinoshita, M.⁴

64
- 0019445634
- e) carbomycin: K. C. Nicolaou, M. R. Pavia, S P. Seitz, Tetrahedron Lett. 1979, 2327; K. Tatsuta, Y. Amemiya, S. Maniwa, M. Kinoshita, ibid. 1980, 21, 2837; K C. Nicolaou, S. P. Seitz, M. R. Pavia, J. Am. Chem. Soc. 1981, 103, 1222; K. C. Nicolaou, M. R. Pavia, S. P. Seitz, ibid. 1981, 103, 1224;
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 1222
- Nicolaou, K.C.¹ Seitz, S.P.² Pavia, M.R.³

65
- 0019467942
- e) carbomycin: K. C. Nicolaou, M. R. Pavia, S P. Seitz, Tetrahedron Lett. 1979, 2327; K. Tatsuta, Y. Amemiya, S. Maniwa, M. Kinoshita, ibid. 1980, 21, 2837; K C. Nicolaou, S. P. Seitz, M. R. Pavia, J. Am. Chem. Soc. 1981, 103, 1222; K. C. Nicolaou, M. R. Pavia, S. P. Seitz, ibid. 1981, 103, 1224;
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 1224
- Nicolaou, K.C.¹ Pavia, M.R.² Seitz, S.P.³

66
- 0019979423
- f) tylosin: K. Tatsuta, Y. Amemiya, Y. Kanemura, H. Takahashi, M. Kinoshita, Tetrahedron Lett. 1982, 23, 3375; P. A. Grieco, J. Inanaga, N.-H. Lin, T. Yanami, J. Am. Chem. Soc. 1982, 104, 5781;
- (1982) Tetrahedron Lett. , vol.23 , pp. 3375
- Tatsuta, K.¹ Amemiya, Y.² Kanemura, Y.³ Takahashi, H.⁴ Kinoshita, M.⁵

67
- 0001464148
- f) tylosin: K. Tatsuta, Y. Amemiya, Y. Kanemura, H. Takahashi, M. Kinoshita, Tetrahedron Lett. 1982, 23, 3375; P. A. Grieco, J. Inanaga, N.-H. Lin, T. Yanami, J. Am. Chem. Soc. 1982, 104, 5781;
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 5781
- Grieco, P.A.¹ Inanaga, J.² Lin, N.-H.³ Yanami, T.⁴

68
- 0000215820
- g) maytansin: E. J. Corey, L. O. Weigel, A. R Chamberlin, B. Lipschutz, ibid. 1980, 102, 1439; E. J. Corey, L. O. Weigel, A. R. Chamberlin, H. Cho, D. H. Hua, ibid. 1980, 102, 6613;
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 1439
- Corey, E.J.¹ Weigel, L.O.² Chamberlin, A.R.³ Lipschutz, B.⁴

69
- 0019194911
- g) maytansin: E. J. Corey, L. O. Weigel, A. R Chamberlin, B. Lipschutz, ibid. 1980, 102, 1439; E. J. Corey, L. O. Weigel, A. R. Chamberlin, H. Cho, D. H. Hua, ibid. 1980, 102, 6613;
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 6613
- Corey, E.J.¹ Weigel, L.O.² Chamberlin, A.R.³ Cho, H.⁴ Hua, D.H.⁵

70
- 0019421555
- h) rifamycins: Y. Kishi, Pure Appl. Chem. 1981, 53, 1163; S. Hanessian, J.-R. Pougny, I K. Boessenkool, J. Am Chem. Soc. 1982, 104, 6164; S Masamune, B. Imperiali, D. S. Garvey, ibid. 1982, 104, 5528; S. Hanessian, J.-R. Pougny, I. K. Boessenkool, Tetrahedron 1984, 40, 1289; S. J. Danishefsky, D. C. Myles, D. F. Harvey, J. Am. Chem. Soc. 1987, 109, 862; F. E. Ziegler, W. T. Cain, A. Kneisley, E. P. Stirchak, R. T. Wester, ibid. 1988, 110, 5442; W. R. Roush, A. D. Palkowitz, K. Ando, ibid. 1990, 112, 6348; T. Harada, Y. Kagamihara, S Tanaka, K. Sakamoto, A Oku, J Org. Chem. 1992, 57, 1637; M. Lautens, R K. Belter, Tetrahedron Lett. 1992, 33, 2617;
- (1981) Pure Appl. Chem , vol.53 , pp. 1163
- Kishi, Y.¹

71
- 0020395634
- h) rifamycins: Y. Kishi, Pure Appl. Chem. 1981, 53, 1163; S. Hanessian, J.-R. Pougny, I K. Boessenkool, J. Am Chem. Soc. 1982, 104, 6164; S Masamune, B. Imperiali, D. S. Garvey, ibid. 1982, 104, 5528; S. Hanessian, J.-R. Pougny, I. K. Boessenkool, Tetrahedron 1984, 40, 1289; S. J. Danishefsky, D. C. Myles, D. F. Harvey, J. Am. Chem. Soc. 1987, 109, 862; F. E. Ziegler, W. T. Cain, A. Kneisley, E. P. Stirchak, R. T. Wester, ibid. 1988, 110, 5442; W. R. Roush, A. D. Palkowitz, K. Ando, ibid. 1990, 112, 6348; T. Harada, Y. Kagamihara, S Tanaka, K. Sakamoto, A Oku, J Org. Chem. 1992, 57, 1637; M. Lautens, R K. Belter, Tetrahedron Lett. 1992, 33, 2617;
- (1982) J. Am Chem. Soc. , vol.104 , pp. 6164
- Hanessian, S.¹ Pougny, J.-R.² Boessenkool, I.K.³

72
- 0020444179
- h) rifamycins: Y. Kishi, Pure Appl. Chem. 1981, 53, 1163; S. Hanessian, J.-R. Pougny, I K. Boessenkool, J. Am Chem. Soc. 1982, 104, 6164; S Masamune, B. Imperiali, D. S. Garvey, ibid. 1982, 104, 5528; S. Hanessian, J.-R. Pougny, I. K. Boessenkool, Tetrahedron 1984, 40, 1289; S. J. Danishefsky, D. C. Myles, D. F. Harvey, J. Am. Chem. Soc. 1987, 109, 862; F. E. Ziegler, W. T. Cain, A. Kneisley, E. P. Stirchak, R. T. Wester, ibid. 1988, 110, 5442; W. R. Roush, A. D. Palkowitz, K. Ando, ibid. 1990, 112, 6348; T. Harada, Y. Kagamihara, S Tanaka, K. Sakamoto, A Oku, J Org. Chem. 1992, 57, 1637; M. Lautens, R K. Belter, Tetrahedron Lett. 1992, 33, 2617;
- (1982) J. Am Chem. Soc. , vol.104 , pp. 5528
- Masamune, S.¹ Imperiali, B.² Garvey, D.S.³

73
- 0141997938
- h) rifamycins: Y. Kishi, Pure Appl. Chem. 1981, 53, 1163; S. Hanessian, J.-R. Pougny, I K. Boessenkool, J. Am Chem. Soc. 1982, 104, 6164; S Masamune, B. Imperiali, D. S. Garvey, ibid. 1982, 104, 5528; S. Hanessian, J.-R. Pougny, I. K. Boessenkool, Tetrahedron 1984, 40, 1289; S. J. Danishefsky, D. C. Myles, D. F. Harvey, J. Am. Chem. Soc. 1987, 109, 862; F. E. Ziegler, W. T. Cain, A. Kneisley, E. P. Stirchak, R. T. Wester, ibid. 1988, 110, 5442; W. R. Roush, A. D. Palkowitz, K. Ando, ibid. 1990, 112, 6348; T. Harada, Y. Kagamihara, S Tanaka, K. Sakamoto, A Oku, J Org. Chem. 1992, 57, 1637; M. Lautens, R K. Belter, Tetrahedron Lett. 1992, 33, 2617;
- (1984) Tetrahedron , vol.40 , pp. 1289
- Hanessian, S.¹ Pougny, J.-R.² Boessenkool, I.K.³

74
- 0000040552
- h) rifamycins: Y. Kishi, Pure Appl. Chem. 1981, 53, 1163; S. Hanessian, J.-R. Pougny, I K. Boessenkool, J. Am Chem. Soc. 1982, 104, 6164; S Masamune, B. Imperiali, D. S. Garvey, ibid. 1982, 104, 5528; S. Hanessian, J.-R. Pougny, I. K. Boessenkool, Tetrahedron 1984, 40, 1289; S. J. Danishefsky, D. C. Myles, D. F. Harvey, J. Am. Chem. Soc. 1987, 109, 862; F. E. Ziegler, W. T. Cain, A. Kneisley, E. P. Stirchak, R. T. Wester, ibid. 1988, 110, 5442; W. R. Roush, A. D. Palkowitz, K. Ando, ibid. 1990, 112, 6348; T. Harada, Y. Kagamihara, S Tanaka, K. Sakamoto, A Oku, J Org. Chem. 1992, 57, 1637; M. Lautens, R K. Belter, Tetrahedron Lett. 1992, 33, 2617;
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 862
- Danishefsky, S.J.¹ Myles, D.C.² Harvey, D.F.³

75
- 0000331350
- h) rifamycins: Y. Kishi, Pure Appl. Chem. 1981, 53, 1163; S. Hanessian, J.-R. Pougny, I K. Boessenkool, J. Am Chem. Soc. 1982, 104, 6164; S Masamune, B. Imperiali, D. S. Garvey, ibid. 1982, 104, 5528; S. Hanessian, J.-R. Pougny, I. K. Boessenkool, Tetrahedron 1984, 40, 1289; S. J. Danishefsky, D. C. Myles, D. F. Harvey, J. Am. Chem. Soc. 1987, 109, 862; F. E. Ziegler, W. T. Cain, A. Kneisley, E. P. Stirchak, R. T. Wester, ibid. 1988, 110, 5442; W. R. Roush, A. D. Palkowitz, K. Ando, ibid. 1990, 112, 6348; T. Harada, Y. Kagamihara, S Tanaka, K. Sakamoto, A Oku, J Org. Chem. 1992, 57, 1637; M. Lautens, R K. Belter, Tetrahedron Lett. 1992, 33, 2617;
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 5442
- Ziegler, F.E.¹ Cain, W.T.² Kneisley, A.³ Stirchak, E.P.⁴ Wester, R.T.⁵

76
- 0025128154
- h) rifamycins: Y. Kishi, Pure Appl. Chem. 1981, 53, 1163; S. Hanessian, J.-R. Pougny, I K. Boessenkool, J. Am Chem. Soc. 1982, 104, 6164; S Masamune, B. Imperiali, D. S. Garvey, ibid. 1982, 104, 5528; S. Hanessian, J.-R. Pougny, I. K. Boessenkool, Tetrahedron 1984, 40, 1289; S. J. Danishefsky, D. C. Myles, D. F. Harvey, J. Am. Chem. Soc. 1987, 109, 862; F. E. Ziegler, W. T. Cain, A. Kneisley, E. P. Stirchak, R. T. Wester, ibid. 1988, 110, 5442; W. R. Roush, A. D. Palkowitz, K. Ando, ibid. 1990, 112, 6348; T. Harada, Y. Kagamihara, S Tanaka, K. Sakamoto, A Oku, J Org. Chem. 1992, 57, 1637; M. Lautens, R K. Belter, Tetrahedron Lett. 1992, 33, 2617;
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 6348
- Roush, W.R.¹ Palkowitz, A.D.² Ando, K.³

77
- 0026552920
- h) rifamycins: Y. Kishi, Pure Appl. Chem. 1981, 53, 1163; S. Hanessian, J.-R. Pougny, I K. Boessenkool, J. Am Chem. Soc. 1982, 104, 6164; S Masamune, B. Imperiali, D. S. Garvey, ibid. 1982, 104, 5528; S. Hanessian, J.-R. Pougny, I. K. Boessenkool, Tetrahedron 1984, 40, 1289; S. J. Danishefsky, D. C. Myles, D. F. Harvey, J. Am. Chem. Soc. 1987, 109, 862; F. E. Ziegler, W. T. Cain, A. Kneisley, E. P. Stirchak, R. T. Wester, ibid. 1988, 110, 5442; W. R. Roush, A. D. Palkowitz, K. Ando, ibid. 1990, 112, 6348; T. Harada, Y. Kagamihara, S Tanaka, K. Sakamoto, A Oku, J Org. Chem. 1992, 57, 1637; M. Lautens, R K. Belter, Tetrahedron Lett. 1992, 33, 2617;
- (1992) J Org. Chem. , vol.57 , pp. 1637
- Harada, T.¹ Kagamihara, Y.² Tanaka, S.³ Sakamoto, K.⁴ Oku, A.⁵

78
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80
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81
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82
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83
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84
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85
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86
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87
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88
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89
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90
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91
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92
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