Total synthesis of amphidinolide T4

Angewandte Chemie - International Edition

Volumn 41, Issue 24, 2002, Pages 4763-4766

  Fürstner, Alois ^a   Aïssa, Christophe ^a   Riveiros, Ricardo ^a   Ragot, Jacques ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Macrolides; Metathesis; Natural products; Ruthenium; Total synthesis; Zinc

Indexed keywords

ANTIBIOTICS; CATALYSIS; MARINE APPLICATIONS; SYNTHESIS (CHEMICAL);

PROTOTYPES;

ORGANOMETALLICS;

AMPHIDINOLIDE T; AMPHIDINOLIDE T4; CARBON; FUSED HETEROCYCLIC RINGS; LACTONE; MACROLIDE; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; ATOM; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DINOFLAGELLATE; HYDROGENATION; SYNTHESIS;

ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; DINOFLAGELLIDA; LACTONES; MACROLIDES; MOLECULAR STRUCTURE;

EID: 0037122052     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200290042     Document Type: Article

References (52)

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8. For total syntheses of other amphidinolides see: a) D. R. Williams, W. S. Kissel, J. Am. Chem. Soc. 1998, 120, 11198-11199; (b) D. R. Williams, B. J. Myers, L. Mi, Org. Lett. 2000, 2, 945-948; (c) D. R. Williams, K. G. Meyer, J. Am. Chem. Soc. 2001, 123, 765-766; (d) H. W. Lam, G. Pattenden, Angew. Chem. 2002, 114, 526-529; Angew. Chem. Int. Ed. 2002, 41, 508-511; (e) T. K. Chakraborty, S. Das, Tetrahedron Lett. 2001, 42, 3387-3390; (f) R. E. Maleczka, L. R. Terrell, F. Geng, J. S. Ward, Org. Lett. 2002, 4, 2841-2844; (g) B. M. Trost, J. D. Chisholm, S. T. Wrobleski, M. Jung, J. Am. Chem. Soc. 2002, 124, 12420-12421.
9. For total syntheses of other amphidinolides see: a) D. R. Williams, W. S. Kissel, J. Am. Chem. Soc. 1998, 120, 11198-11199; (b) D. R. Williams, B. J. Myers, L. Mi, Org. Lett. 2000, 2, 945-948; (c) D. R. Williams, K. G. Meyer, J. Am. Chem. Soc. 2001, 123, 765-766; (d) H. W. Lam, G. Pattenden, Angew. Chem. 2002, 114, 526-529; Angew. Chem. Int. Ed. 2002, 41, 508-511; (e) T. K. Chakraborty, S. Das, Tetrahedron Lett. 2001, 42, 3387-3390; (f) R. E. Maleczka, L. R. Terrell, F. Geng, J. S. Ward, Org. Lett. 2002, 4, 2841-2844; (g) B. M. Trost, J. D. Chisholm, S. T. Wrobleski, M. Jung, J. Am. Chem. Soc. 2002, 124, 12420-12421.
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36. These expectations stem from results in the following projects: a) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; (b) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; (c) A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5284-5296; (d) A. Fürstner, O. R. Thiel, N. Kindler, B. Bartkowska, J. Org. Chem. 2000, 65, 7990-7995; (e) A. Fürstner, T. Müller, J. Am. Chem. Soc. 1999, 121, 7814-7821; (f) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130-9136; (g) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943.
37. These expectations stem from results in the following projects: a) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; (b) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; (c) A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5284-5296; (d) A. Fürstner, O. R. Thiel, N. Kindler, B. Bartkowska, J. Org. Chem. 2000, 65, 7990-7995; (e) A. Fürstner, T. Müller, J. Am. Chem. Soc. 1999, 121, 7814-7821; (f) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130-9136; (g) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943.
38. These expectations stem from results in the following projects: a) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; (b) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; (c) A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5284-5296; (d) A. Fürstner, O. R. Thiel, N. Kindler, B. Bartkowska, J. Org. Chem. 2000, 65, 7990-7995; (e) A. Fürstner, T. Müller, J. Am. Chem. Soc. 1999, 121, 7814-7821; (f) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130-9136; (g) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943.
39. These expectations stem from results in the following projects: a) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; (b) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; (c) A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5284-5296; (d) A. Fürstner, O. R. Thiel, N. Kindler, B. Bartkowska, J. Org. Chem. 2000, 65, 7990-7995; (e) A. Fürstner, T. Müller, J. Am. Chem. Soc. 1999, 121, 7814-7821; (f) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130-9136; (g) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943.
40. These expectations stem from results in the following projects: a) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; (b) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; (c) A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5284-5296; (d) A. Fürstner, O. R. Thiel, N. Kindler, B. Bartkowska, J. Org. Chem. 2000, 65, 7990-7995; (e) A. Fürstner, T. Müller, J. Am. Chem. Soc. 1999, 121, 7814-7821; (f) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130-9136; (g) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943.
41. These expectations stem from results in the following projects: a) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; (b) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; (c) A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5284-5296; (d) A. Fürstner, O. R. Thiel, N. Kindler, B. Bartkowska, J. Org. Chem. 2000, 65, 7990-7995; (e) A. Fürstner, T. Müller, J. Am. Chem. Soc. 1999, 121, 7814-7821; (f) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130-9136; (g) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943.
42. These expectations stem from results in the following projects: a) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; (b) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; (c) A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5284-5296; (d) A. Fürstner, O. R. Thiel, N. Kindler, B. Bartkowska, J. Org. Chem. 2000, 65, 7990-7995; (e) A. Fürstner, T. Müller, J. Am. Chem. Soc. 1999, 121, 7814-7821; (f) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130-9136; (g) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943.
43. These expectations stem from results in the following projects: a) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; (b) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; (c) A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5284-5296; (d) A. Fürstner, O. R. Thiel, N. Kindler, B. Bartkowska, J. Org. Chem. 2000, 65, 7990-7995; (e) A. Fürstner, T. Müller, J. Am. Chem. Soc. 1999, 121, 7814-7821; (f) A. Fürstner, K. Langemann, J. Am. Chem. Soc. 1997, 119, 9130-9136; (g) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943.
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46. (c) L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A. Herrmann, Tetrahedron Lett. 1999, 40, 4787-4790;
47. (d) A. Fürstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer, O. R. Thiel, Chem. Eur. J. 2001, 7, 3236-3253.
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