Efficient total syntheses of resin glycosides and analogues by ring- closing olefin metathesis

Journal of the American Chemical Society

Volumn 121, Issue 34, 1999, Pages 7814-7821

  Fürstner, Alois ^a   Müller, Thomas ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE; ALLENE DERIVATIVE; DISACCHARIDE; FLUOROFORM; GLYCOLIPID; GLYCOSIDE; HYDROXYL GROUP; LACTONE DERIVATIVE; MACROCYCLIC COMPOUND; NATURAL PRODUCT; OLIGOSACCHARIDE; RESIN; RUTHENIUM DERIVATIVE; SULFONAMIDE; TITANIUM DERIVATIVE; UNDECANOL;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038528214     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991361l     Document Type: Article

References (96)

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21. For yet other families of resin glycosides see the following for leading references: (a) MacLeod, J. K.; Ward, A.; Oelrichs, P. B. J. Nat. Prod. 1997, 60, 467. (b) Kitagawa, I.; Baek, N. I.; Kawashima, K.; Yokokawa, Y.; Yoshikawa, M.; Ohasni, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1680. (c) Noda, N.; Tsuji, K.; Kawasaki, T.; Miyahara, K.; Hanazono, H.; Yang, C.-R. Chem. Pharm. Bull. 1995, 43, 1061. (d) Noda, N.; Kobayashi, H.; Miyahara, K.; Kawasaki, T. Chem. Pharm. Bull. 1988, 36, 920. (e) Kitagawa, I.; Baek, N. I.; Yokokawa, Y.; Yoshikawa, M.; Ohashi, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1693. (f) Fang, Y.- W.; Chai, W.-R.; Chen, S.-M.; He, Y.-Z.; Zhao, L.; Peng, J.-H.; Huang, H.-W.; Xin, B. Carbohydr. Res. 1993, 245, 259.
22. For yet other families of resin glycosides see the following for leading references: (a) MacLeod, J. K.; Ward, A.; Oelrichs, P. B. J. Nat. Prod. 1997, 60, 467. (b) Kitagawa, I.; Baek, N. I.; Kawashima, K.; Yokokawa, Y.; Yoshikawa, M.; Ohasni, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1680. (c) Noda, N.; Tsuji, K.; Kawasaki, T.; Miyahara, K.; Hanazono, H.; Yang, C.-R. Chem. Pharm. Bull. 1995, 43, 1061. (d) Noda, N.; Kobayashi, H.; Miyahara, K.; Kawasaki, T. Chem. Pharm. Bull. 1988, 36, 920. (e) Kitagawa, I.; Baek, N. I.; Yokokawa, Y.; Yoshikawa, M.; Ohashi, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1693. (f) Fang, Y.- W.; Chai, W.-R.; Chen, S.-M.; He, Y.-Z.; Zhao, L.; Peng, J.-H.; Huang, H.-W.; Xin, B. Carbohydr. Res. 1993, 245, 259.
23. For yet other families of resin glycosides see the following for leading references: (a) MacLeod, J. K.; Ward, A.; Oelrichs, P. B. J. Nat. Prod. 1997, 60, 467. (b) Kitagawa, I.; Baek, N. I.; Kawashima, K.; Yokokawa, Y.; Yoshikawa, M.; Ohasni, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1680. (c) Noda, N.; Tsuji, K.; Kawasaki, T.; Miyahara, K.; Hanazono, H.; Yang, C.-R. Chem. Pharm. Bull. 1995, 43, 1061. (d) Noda, N.; Kobayashi, H.; Miyahara, K.; Kawasaki, T. Chem. Pharm. Bull. 1988, 36, 920. (e) Kitagawa, I.; Baek, N. I.; Yokokawa, Y.; Yoshikawa, M.; Ohashi, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1693. (f) Fang, Y.- W.; Chai, W.-R.; Chen, S.-M.; He, Y.-Z.; Zhao, L.; Peng, J.-H.; Huang, H.-W.; Xin, B. Carbohydr. Res. 1993, 245, 259.
24. For yet other families of resin glycosides see the following for leading references: (a) MacLeod, J. K.; Ward, A.; Oelrichs, P. B. J. Nat. Prod. 1997, 60, 467. (b) Kitagawa, I.; Baek, N. I.; Kawashima, K.; Yokokawa, Y.; Yoshikawa, M.; Ohasni, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1680. (c) Noda, N.; Tsuji, K.; Kawasaki, T.; Miyahara, K.; Hanazono, H.; Yang, C.-R. Chem. Pharm. Bull. 1995, 43, 1061. (d) Noda, N.; Kobayashi, H.; Miyahara, K.; Kawasaki, T. Chem. Pharm. Bull. 1988, 36, 920. (e) Kitagawa, I.; Baek, N. I.; Yokokawa, Y.; Yoshikawa, M.; Ohashi, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1693. (f) Fang, Y.- W.; Chai, W.-R.; Chen, S.-M.; He, Y.-Z.; Zhao, L.; Peng, J.-H.; Huang, H.-W.; Xin, B. Carbohydr. Res. 1993, 245, 259.
25. For yet other families of resin glycosides see the following for leading references: (a) MacLeod, J. K.; Ward, A.; Oelrichs, P. B. J. Nat. Prod. 1997, 60, 467. (b) Kitagawa, I.; Baek, N. I.; Kawashima, K.; Yokokawa, Y.; Yoshikawa, M.; Ohasni, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1680. (c) Noda, N.; Tsuji, K.; Kawasaki, T.; Miyahara, K.; Hanazono, H.; Yang, C.-R. Chem. Pharm. Bull. 1995, 43, 1061. (d) Noda, N.; Kobayashi, H.; Miyahara, K.; Kawasaki, T. Chem. Pharm. Bull. 1988, 36, 920. (e) Kitagawa, I.; Baek, N. I.; Yokokawa, Y.; Yoshikawa, M.; Ohashi, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1693. (f) Fang, Y.-W.; Chai, W.-R.; Chen, S.-M.; He, Y.-Z.; Zhao, L.; Peng, J.-H.; Huang, H.-W.; Xin, B. Carbohydr. Res. 1993, 245, 259.
26. Although most resin glycosides have been isolated from plants (Convolvulaceae), scattered reports on the isolation of related glycolipids from bacteria, fungi, and yeasts can be found in the literature, some of which contain fatty acid components other than jalapinolic acid as the aglycon. For an extensive compilation of relevant literature on the isolation, structure, and biological properties of such glycolipids see the following for leading references: (a) Bisht, K. S.; Gross, R. A.; Kaplan, D. L. J. Org. Chem. 1999, 64, 780. (b) See also: Legler, G. Photochemistry 1965, 4, 29. (c) Wagner, H.; Kazmaier, P. Tetrahedron Lett. 1971, 12, 3233. (d) Kawasaki, T.; Okabe, H.; Nakatsuka, I. Chem. Pharm. Bull. 1971, 19, 1144 and literature cited therein. (e) Key, B. A.; Gray, G. W.; Wilkinson, S. G. Biochem. J. 1970, 13, 593. (f) Hirayama, T.; Kato, I. FEBS Lett. 1982, 139, 81. (g) Weber, L.; Stach, J.; Haufe, G.; Hommel, R.: Kleber, H.-P. Carbohydr. Res. 1990, 206, 13. (h) Asmer, H. J.; Lang, S.; Wagner, F.; Wray, V. J. Am. Oil Soc. 1988, 65, 1460.
27. Although most resin glycosides have been isolated from plants (Convolvulaceae), scattered reports on the isolation of related glycolipids from bacteria, fungi, and yeasts can be found in the literature, some of which contain fatty acid components other than jalapinolic acid as the aglycon. For an extensive compilation of relevant literature on the isolation, structure, and biological properties of such glycolipids see the following for leading references: (a) Bisht, K. S.; Gross, R. A.; Kaplan, D. L. J. Org. Chem. 1999, 64, 780. (b) See also: Legler, G. Photochemistry 1965, 4, 29. (c) Wagner, H.; Kazmaier, P. Tetrahedron Lett. 1971, 12, 3233. (d) Kawasaki, T.; Okabe, H.; Nakatsuka, I. Chem. Pharm. Bull. 1971, 19, 1144 and literature cited therein. (e) Key, B. A.; Gray, G. W.; Wilkinson, S. G. Biochem. J. 1970, 13, 593. (f) Hirayama, T.; Kato, I. FEBS Lett. 1982, 139, 81. (g) Weber, L.; Stach, J.; Haufe, G.; Hommel, R.: Kleber, H.-P. Carbohydr. Res. 1990, 206, 13. (h) Asmer, H. J.; Lang, S.; Wagner, F.; Wray, V. J. Am. Oil Soc. 1988, 65, 1460.
28. Although most resin glycosides have been isolated from plants (Convolvulaceae), scattered reports on the isolation of related glycolipids from bacteria, fungi, and yeasts can be found in the literature, some of which contain fatty acid components other than jalapinolic acid as the aglycon. For an extensive compilation of relevant literature on the isolation, structure, and biological properties of such glycolipids see the following for leading references: (a) Bisht, K. S.; Gross, R. A.; Kaplan, D. L. J. Org. Chem. 1999, 64, 780. (b) See also: Legler, G. Photochemistry 1965, 4, 29. (c) Wagner, H.; Kazmaier, P. Tetrahedron Lett. 1971, 12, 3233. (d) Kawasaki, T.; Okabe, H.; Nakatsuka, I. Chem. Pharm. Bull. 1971, 19, 1144 and literature cited therein. (e) Key, B. A.; Gray, G. W.; Wilkinson, S. G. Biochem. J. 1970, 13, 593. (f) Hirayama, T.; Kato, I. FEBS Lett. 1982, 139, 81. (g) Weber, L.; Stach, J.; Haufe, G.; Hommel, R.: Kleber, H.-P. Carbohydr. Res. 1990, 206, 13. (h) Asmer, H. J.; Lang, S.; Wagner, F.; Wray, V. J. Am. Oil Soc. 1988, 65, 1460.
29. Although most resin glycosides have been isolated from plants (Convolvulaceae), scattered reports on the isolation of related glycolipids from bacteria, fungi, and yeasts can be found in the literature, some of which contain fatty acid components other than jalapinolic acid as the aglycon. For an extensive compilation of relevant literature on the isolation, structure, and biological properties of such glycolipids see the following for leading references: (a) Bisht, K. S.; Gross, R. A.; Kaplan, D. L. J. Org. Chem. 1999, 64, 780. (b) See also: Legler, G. Photochemistry 1965, 4, 29. (c) Wagner, H.; Kazmaier, P. Tetrahedron Lett. 1971, 12, 3233. (d) Kawasaki, T.; Okabe, H.; Nakatsuka, I. Chem. Pharm. Bull. 1971, 19, 1144 and literature cited therein. (e) Key, B. A.; Gray, G. W.; Wilkinson, S. G. Biochem. J. 1970, 13, 593. (f) Hirayama, T.; Kato, I. FEBS Lett. 1982, 139, 81. (g) Weber, L.; Stach, J.; Haufe, G.; Hommel, R.: Kleber, H.-P. Carbohydr. Res. 1990, 206, 13. (h) Asmer, H. J.; Lang, S.; Wagner, F.; Wray, V. J. Am. Oil Soc. 1988, 65, 1460.
30. Although most resin glycosides have been isolated from plants (Convolvulaceae), scattered reports on the isolation of related glycolipids from bacteria, fungi, and yeasts can be found in the literature, some of which contain fatty acid components other than jalapinolic acid as the aglycon. For an extensive compilation of relevant literature on the isolation, structure, and biological properties of such glycolipids see the following for leading references: (a) Bisht, K. S.; Gross, R. A.; Kaplan, D. L. J. Org. Chem. 1999, 64, 780. (b) See also: Legler, G. Photochemistry 1965, 4, 29. (c) Wagner, H.; Kazmaier, P. Tetrahedron Lett. 1971, 12, 3233. (d) Kawasaki, T.; Okabe, H.; Nakatsuka, I. Chem. Pharm. Bull. 1971, 19, 1144 and literature cited therein. (e) Key, B. A.; Gray, G. W.; Wilkinson, S. G. Biochem. J. 1970, 13, 593. (f) Hirayama, T.; Kato, I. FEBS Lett. 1982, 139, 81. (g) Weber, L.; Stach, J.; Haufe, G.; Hommel, R.: Kleber, H.-P. Carbohydr. Res. 1990, 206, 13. (h) Asmer, H. J.; Lang, S.; Wagner, F.; Wray, V. J. Am. Oil Soc. 1988, 65, 1460.
31. Although most resin glycosides have been isolated from plants (Convolvulaceae), scattered reports on the isolation of related glycolipids from bacteria, fungi, and yeasts can be found in the literature, some of which contain fatty acid components other than jalapinolic acid as the aglycon. For an extensive compilation of relevant literature on the isolation, structure, and biological properties of such glycolipids see the following for leading references: (a) Bisht, K. S.; Gross, R. A.; Kaplan, D. L. J. Org. Chem. 1999, 64, 780. (b) See also: Legler, G. Photochemistry 1965, 4, 29. (c) Wagner, H.; Kazmaier, P. Tetrahedron Lett. 1971, 12, 3233. (d) Kawasaki, T.; Okabe, H.; Nakatsuka, I. Chem. Pharm. Bull. 1971, 19, 1144 and literature cited therein. (e) Key, B. A.; Gray, G. W.; Wilkinson, S. G. Biochem. J. 1970, 13, 593. (f) Hirayama, T.; Kato, I. FEBS Lett. 1982, 139, 81. (g) Weber, L.; Stach, J.; Haufe, G.; Hommel, R.: Kleber, H.-P. Carbohydr. Res. 1990, 206, 13. (h) Asmer, H. J.; Lang, S.; Wagner, F.; Wray, V. J. Am. Oil Soc. 1988, 65, 1460.
32. Although most resin glycosides have been isolated from plants (Convolvulaceae), scattered reports on the isolation of related glycolipids from bacteria, fungi, and yeasts can be found in the literature, some of which contain fatty acid components other than jalapinolic acid as the aglycon. For an extensive compilation of relevant literature on the isolation, structure, and biological properties of such glycolipids see the following for leading references: (a) Bisht, K. S.; Gross, R. A.; Kaplan, D. L. J. Org. Chem. 1999, 64, 780. (b) See also: Legler, G. Photochemistry 1965, 4, 29. (c) Wagner, H.; Kazmaier, P. Tetrahedron Lett. 1971, 12, 3233. (d) Kawasaki, T.; Okabe, H.; Nakatsuka, I. Chem. Pharm. Bull. 1971, 19, 1144 and literature cited therein. (e) Key, B. A.; Gray, G. W.; Wilkinson, S. G. Biochem. J. 1970, 13, 593. (f) Hirayama, T.; Kato, I. FEBS Lett. 1982, 139, 81. (g) Weber, L.; Stach, J.; Haufe, G.; Hommel, R.: Kleber, H.-P. Carbohydr. Res. 1990, 206, 13. (h) Asmer, H. J.; Lang, S.; Wagner, F.; Wray, V. J. Am. Oil Soc. 1988, 65, 1460.
33. Although most resin glycosides have been isolated from plants (Convolvulaceae), scattered reports on the isolation of related glycolipids from bacteria, fungi, and yeasts can be found in the literature, some of which contain fatty acid components other than jalapinolic acid as the aglycon. For an extensive compilation of relevant literature on the isolation, structure, and biological properties of such glycolipids see the following for leading references: (a) Bisht, K. S.; Gross, R. A.; Kaplan, D. L. J. Org. Chem. 1999, 64, 780. (b) See also: Legler, G. Photochemistry 1965, 4, 29. (c) Wagner, H.; Kazmaier, P. Tetrahedron Lett. 1971, 12, 3233. (d) Kawasaki, T.; Okabe, H.; Nakatsuka, I. Chem. Pharm. Bull. 1971, 19, 1144 and literature cited therein. (e) Key, B. A.; Gray, G. W.; Wilkinson, S. G. Biochem. J. 1970, 13, 593. (f) Hirayama, T.; Kato, I. FEBS Lett. 1982, 139, 81. (g) Weber, L.; Stach, J.; Haufe, G.; Hommel, R.: Kleber, H.-P. Carbohydr. Res. 1990, 206, 13. (h) Asmer, H. J.; Lang, S.; Wagner, F.; Wray, V. J. Am. Oil Soc. 1988, 65, 1460.
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41. For a preliminary communication see: Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424.
42. For recent reviews on RCM see the following for leading references: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997,4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. Top. Organomet. Chem. 1998, 1, 37.
43. For recent reviews on RCM see the following for leading references: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997,4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. Top. Organomet. Chem. 1998, 1, 37.
44. For recent reviews on RCM see the following for leading references: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997,4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. Top. Organomet. Chem. 1998, 1, 37.
45. For recent reviews on RCM see the following for leading references: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Top. Catal. 1997,4, 285. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (d) Fürstner, A. Top. Organomet. Chem. 1998, 1, 37.
46. For RCM-based macrocycle syntheses from our laboratory see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792-803. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361. (h) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215.
47. For RCM-based macrocycle syntheses from our laboratory see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792-803. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361. (h) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215.
48. For RCM-based macrocycle syntheses from our laboratory see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792-803. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361. (h) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215.
49. For RCM-based macrocycle syntheses from our laboratory see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792-803. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361. (h) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215.
50. For RCM-based macrocycle syntheses from our laboratory see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792-803. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361. (h) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215.
51. For RCM-based macrocycle syntheses from our laboratory see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792-803. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361. (h) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215.
52. For RCM-based macrocycle syntheses from our laboratory see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792-803. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361. (h) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215.
53. For RCM-based macrocycle syntheses from our laboratory see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942. (b) Fürstner, A.; Langemann, K. Synthesis 1997, 792-803. (c) Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 8746. (e) Fürstner, A.; Müller, T. Synlett 1997, 1010. (f) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130. (g) Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361. (h) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215.
54. For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73. (b) Hoveyda, A. H. Top. Organomet. Chem. 1998, 1, 105. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (e) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866. (f) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837. (g) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (h) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587. (i) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741. (j) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
55. For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73. (b) Hoveyda, A. H. Top. Organomet. Chem. 1998, 1, 105. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (e) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866. (f) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837. (g) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (h) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587. (i) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741. (j) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
56. For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73. (b) Hoveyda, A. H. Top. Organomet. Chem. 1998, 1, 105. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (e) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866. (f) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837. (g) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (h) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587. (i) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741. (j) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
57. For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73. (b) Hoveyda, A. H. Top. Organomet. Chem. 1998, 1, 105. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (e) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866. (f) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837. (g) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (h) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587. (i) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741. (j) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
58. For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73. (b) Hoveyda, A. H. Top. Organomet. Chem. 1998, 1, 105. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (e) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866. (f) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837. (g) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (h) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587. (i) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741. (j) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
59. For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73. (b) Hoveyda, A. H. Top. Organomet. Chem. 1998, 1, 105. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (e) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866. (f) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837. (g) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (h) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587. (i) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741. (j) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
60. For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73. (b) Hoveyda, A. H. Top. Organomet. Chem. 1998, 1, 105. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (e) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866. (f) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837. (g) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (h) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587. (i) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741. (j) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
61. For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73. (b) Hoveyda, A. H. Top. Organomet. Chem. 1998, 1, 105. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (e) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866. (f) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837. (g) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (h) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587. (i) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741. (j) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
62. For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73. (b) Hoveyda, A. H. Top. Organomet. Chem. 1998, 1, 105. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (e) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866. (f) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837. (g) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (h) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587. (i) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741. (j) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
63. For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73. (b) Hoveyda, A. H. Top. Organomet. Chem. 1998, 1, 105. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (e) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866. (f) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 837. (g) Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601. (h) Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587. (i) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741. (j) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
64. (a) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691.
65. (b) Knochel, P. In Active Metals. Preparation, Characterization, Applications; Fürstner, A., Ed.; VCH: Weinheim, 1996; p 191.
66. (c) Knochel, P. Synlett 1995, 393.
67. (d) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; p 255.
68. 2 at 0°C → room temperature; cf. Nicolaou, K. C.; Hummel, C. W.; Nakada, M.; Shibayama, K.; Pitsinos, E. N.; Saimoto, H.; Mizuno, Y.; Baldenius, K.-U.; Smith, A. L. J. Am. Chem. Soc. 1993, 115, 7625.
69. Van Boeckel, C. A. A.; Beetz, T.; Kock-van Dalen, A. C.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1987, 106, 596.
70. Barili, P. L.; Berti, G.; Catelani, G.; Cini, C.; D'Andrea, F.; Mastrorilli, E. Carbohydr. Res. 1995, 278, 43.
71. For pertinent reviews on the trichloroacetimidate method see: (a) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (b) Schmidt, R. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, p 33. (c) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
72. For pertinent reviews on the trichloroacetimidate method see: (a) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (b) Schmidt, R. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, p 33. (c) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
73. For pertinent reviews on the trichloroacetimidate method see: (a) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (b) Schmidt, R. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, p 33. (c) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
74. For pertinent reviews on the trichloroacetimidate method see: (a) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (b) Schmidt, R. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, p 33. (c) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
75. (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858.
76. (b) See also: Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2179.
77. A full report on the X-ray structure of compound 21 can be found in Lehmann, C. W.; Rust, J.; Fürstner, A., Müller, T. Z. Kristallogr., submitted for publication.
78. (a) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95.
79. (b) Fürstner, A.; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315.
80. (c) See also: Fürstner, A.; Hill, A. F.; Liebl, M.; Winton-Ely, J. D. E. T. Chem. Commun. 1999, 601.
81. 2 is activated by the ruthenium complex, thus serving as the actual carbene source. See the following for a leading reference on the formation of ruthenium carbene complexes by oxidative insertion into gem-dihaloalkanes: Belderrain, T. R.; Grubbs, R. H. Organometallics 1997, 16, 4001.
82. 2 at 0°C → room temperature; cf. Experimental Section.
83. The same sequence of reactions using D-glucose instead of L-rhamnose as the starting material was used during a recent total synthesis of caloporoside; cf. Fürstner, A.; Konetzki, I. J. Org. Chem. 1998, 63, 3072.
84. Fürstner, A.; Konetzki, I. Tetrahedron Lett. 1998, 39, 5721.
85. David, S. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997; p 69.
86. The epothilone case constitutes a most notable precedent for this conclusion. For extensive reviews on how the SAR of this promising anticancer agent has been established using RCM-based synthesis strategies see ref 19a,d,j and the following for leading references: (a) Nicolaou; K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014. (b) Nicolaou, K. C.; He, Y.; Roschanger, F.; King, N. P.; Vourloumis, D.; Li, T. Angew. Chem., Int. Ed. Engl. 1998, 37, 84. (c) Nicolaou, K. C., Vallberg, H.; King, N. P.; Roschanger, F.; He, Y.; Vourloumis, D.; Nicolaou, C. G. Chem. Eur. J. 1997, 3, 1957. (d) Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Wissinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschanger, F.; King, N. P., Finlay, M. R. V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2097. (e) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073. (f) Su, D.-S.; Balog, A.; Meng, D.; Bertinato, P.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2093 and literature cited therein.
87. The epothilone case constitutes a most notable precedent for this conclusion. For extensive reviews on how the SAR of this promising anticancer agent has been established using RCM-based synthesis strategies see ref 19a,d,j and the following for leading references: (a) Nicolaou; K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014. (b) Nicolaou, K. C.; He, Y.; Roschanger, F.; King, N. P.; Vourloumis, D.; Li, T. Angew. Chem., Int. Ed. Engl. 1998, 37, 84. (c) Nicolaou, K. C., Vallberg, H.; King, N. P.; Roschanger, F.; He, Y.; Vourloumis, D.; Nicolaou, C. G. Chem. Eur. J. 1997, 3, 1957. (d) Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Wissinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschanger, F.; King, N. P., Finlay, M. R. V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2097. (e) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073. (f) Su, D.-S.; Balog, A.; Meng, D.; Bertinato, P.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2093 and literature cited therein.
88. The epothilone case constitutes a most notable precedent for this conclusion. For extensive reviews on how the SAR of this promising anticancer agent has been established using RCM-based synthesis strategies see ref 19a,d,j and the following for leading references: (a) Nicolaou; K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014. (b) Nicolaou, K. C.; He, Y.; Roschanger, F.; King, N. P.; Vourloumis, D.; Li, T. Angew. Chem., Int. Ed. Engl. 1998, 37, 84. (c) Nicolaou, K. C., Vallberg, H.; King, N. P.; Roschanger, F.; He, Y.; Vourloumis, D.; Nicolaou, C. G. Chem. Eur. J. 1997, 3, 1957. (d) Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Wissinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschanger, F.; King, N. P., Finlay, M. R. V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2097. (e) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073. (f) Su, D.-S.; Balog, A.; Meng, D.; Bertinato, P.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2093 and literature cited therein.
89. The epothilone case constitutes a most notable precedent for this conclusion. For extensive reviews on how the SAR of this promising anticancer agent has been established using RCM-based synthesis strategies see ref 19a,d,j and the following for leading references: (a) Nicolaou; K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014. (b) Nicolaou, K. C.; He, Y.; Roschanger, F.; King, N. P.; Vourloumis, D.; Li, T. Angew. Chem., Int. Ed. Engl. 1998, 37, 84. (c) Nicolaou, K. C., Vallberg, H.; King, N. P.; Roschanger, F.; He, Y.; Vourloumis, D.; Nicolaou, C. G. Chem. Eur. J. 1997, 3, 1957. (d) Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Wissinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschanger, F.; King, N. P., Finlay, M. R. V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2097. (e) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073. (f) Su, D.-S.; Balog, A.; Meng, D.; Bertinato, P.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2093 and literature cited therein.
90. The epothilone case constitutes a most notable precedent for this conclusion. For extensive reviews on how the SAR of this promising anticancer agent has been established using RCM-based synthesis strategies see ref 19a,d,j and the following for leading references: (a) Nicolaou; K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014. (b) Nicolaou, K. C.; He, Y.; Roschanger, F.; King, N. P.; Vourloumis, D.; Li, T. Angew. Chem., Int. Ed. Engl. 1998, 37, 84. (c) Nicolaou, K. C., Vallberg, H.; King, N. P.; Roschanger, F.; He, Y.; Vourloumis, D.; Nicolaou, C. G. Chem. Eur. J. 1997, 3, 1957. (d) Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Wissinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschanger, F.; King, N. P., Finlay, M. R. V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2097. (e) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073. (f) Su, D.-S.; Balog, A.; Meng, D.; Bertinato, P.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2093 and literature cited therein.
91. The epothilone case constitutes a most notable precedent for this conclusion. For extensive reviews on how the SAR of this promising anticancer agent has been established using RCM-based synthesis strategies see ref 19a,d,j and the following for leading references: (a) Nicolaou; K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014. (b) Nicolaou, K. C.; He, Y.; Roschanger, F.; King, N. P.; Vourloumis, D.; Li, T. Angew. Chem., Int. Ed. Engl. 1998, 37, 84. (c) Nicolaou, K. C., Vallberg, H.; King, N. P.; Roschanger, F.; He, Y.; Vourloumis, D.; Nicolaou, C. G. Chem. Eur. J. 1997, 3, 1957. (d) Nicolaou, K. C.; Vourloumis, D.; Li, T.; Pastor, J.; Wissinger, N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschanger, F.; King, N. P., Finlay, M. R. V.; Giannakakou, P.; Verdier-Pinard, P.; Hamel, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2097. (e) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073. (f) Su, D.-S.; Balog, A.; Meng, D.; Bertinato, P.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2093 and literature cited therein.
92. (a) For the first examples of ring-closing diyne metathesis see: Fürstner, A.; Seidel, G. Angew. Chem. 1998, 110, 1758; Angew. Chem., Int. Ed. Engl. 1998, 37, 1734. (b) For Pt(II)-catalyzed enyne metathesis reactions see: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305. (c) For metathesis in supercritical carbon dioxide see: Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem., Int. Ed. Engl. 1997, 36, 2466.
93. (a) For the first examples of ring-closing diyne metathesis see: Fürstner, A.; Seidel, G. Angew. Chem. 1998, 110, 1758; Angew. Chem., Int. Ed. Engl. 1998, 37, 1734. (b) For Pt(II)-catalyzed enyne metathesis reactions see: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305. (c) For metathesis in supercritical carbon dioxide see: Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem., Int. Ed. Engl. 1997, 36, 2466.
94. (a) For the first examples of ring-closing diyne metathesis see: Fürstner, A.; Seidel, G. Angew. Chem. 1998, 110, 1758; Angew. Chem., Int. Ed. Engl. 1998, 37, 1734. (b) For Pt(II)-catalyzed enyne metathesis reactions see: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305. (c) For metathesis in supercritical carbon dioxide see: Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem., Int. Ed. Engl. 1997, 36, 2466.
95. (a) For the first examples of ring-closing diyne metathesis see: Fürstner, A.; Seidel, G. Angew. Chem. 1998, 110, 1758; Angew. Chem., Int. Ed. Engl. 1998, 37, 1734. (b) For Pt(II)-catalyzed enyne metathesis reactions see: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305. (c) For metathesis in supercritical carbon dioxide see: Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem., Int. Ed. Engl. 1997, 36, 2466.
96. (a) For the first examples of ring-closing diyne metathesis see: Fürstner, A.; Seidel, G. Angew. Chem. 1998, 110, 1758; Angew. Chem., Int. Ed. Engl. 1998, 37, 1734. (b) For Pt(II)-catalyzed enyne metathesis reactions see: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305. (c) For metathesis in supercritical carbon dioxide see: Fürstner, A.; Koch, D.; Langemann, K.; Leitner, W.; Six, C. Angew. Chem. 1997, 109, 2562; Angew. Chem., Int. Ed. Engl. 1997, 36, 2466.