Chemical biology of epothilones

Angewandte Chemie - International Edition

Volumn 37, Issue 15, 1998, Pages 2014-2045

  Nicolaou, K C ^a,b   Roschangar, Frank ^a,b   Vourloumis, Dionisios ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Antitumor agents; Epothilones; Natural products; Structure activity relationships; Total synthesis

Indexed keywords

EID: 0032541259     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980817)37:15<2014::AID-ANIE2014>3.0.CO;2-2     Document Type: Review

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144. Total synthesis: a) J. B. Nerenberg, D. T. Hung, P. K. Somers, S. L. Schreiber, J. Am. Chem. Soc. 1993, 115, 12621-12622; b) A. B. Smith III, Y. Qiu, D. R. Jones, K. Kobayashi, J. Am. Chem. Soc. 1995, 117, 12011-12012; c) S. S. Harried, G. Yang, M. A. Strawn, D. C. Myles, J. Org. Chem. 1997, 62, 6098-6099; biological activity: d) E. ter Haar, R. J. Kowalski, E. Hamel, M. C. Lin, R. E. Longley, S. P. Gunasekera, H. S. Rosenkranz, B. W. Day, Biochem. 1996, 35, 243-250; e) D. T. Hung, J. Chen, S. L. Schreiber, Chem. Biol. 1996, 3, 287-293; f) R. J. Kowalski, P. Giannakakou, S. P. Gunasekera, R. E. Longley, B. W. Day, E. Hamel, Mol. Pharmacol. 1997, 52, 613-622; isolation: g) S. P. Gunasekera, M. Gunasekera, R. E. Longley, G. K. Schulte, J. org. Chem. 1990, 55, 4912-4915.
145. Total synthesis: a) J. B. Nerenberg, D. T. Hung, P. K. Somers, S. L. Schreiber, J. Am. Chem. Soc. 1993, 115, 12621-12622; b) A. B. Smith III, Y. Qiu, D. R. Jones, K. Kobayashi, J. Am. Chem. Soc. 1995, 117, 12011-12012; c) S. S. Harried, G. Yang, M. A. Strawn, D. C. Myles, J. Org. Chem. 1997, 62, 6098-6099; biological activity: d) E. ter Haar, R. J. Kowalski, E. Hamel, M. C. Lin, R. E. Longley, S. P. Gunasekera, H. S. Rosenkranz, B. W. Day, Biochem. 1996, 35, 243-250; e) D. T. Hung, J. Chen, S. L. Schreiber, Chem. Biol. 1996, 3, 287-293; f) R. J. Kowalski, P. Giannakakou, S. P. Gunasekera, R. E. Longley, B. W. Day, E. Hamel, Mol. Pharmacol. 1997, 52, 613-622; isolation: g) S. P. Gunasekera, M. Gunasekera, R. E. Longley, G. K. Schulte, J. org. Chem. 1990, 55, 4912-4915.
146. Total synthesis: a) J. B. Nerenberg, D. T. Hung, P. K. Somers, S. L. Schreiber, J. Am. Chem. Soc. 1993, 115, 12621-12622; b) A. B. Smith III, Y. Qiu, D. R. Jones, K. Kobayashi, J. Am. Chem. Soc. 1995, 117, 12011-12012; c) S. S. Harried, G. Yang, M. A. Strawn, D. C. Myles, J. Org. Chem. 1997, 62, 6098-6099; biological activity: d) E. ter Haar, R. J. Kowalski, E. Hamel, M. C. Lin, R. E. Longley, S. P. Gunasekera, H. S. Rosenkranz, B. W. Day, Biochem. 1996, 35, 243-250; e) D. T. Hung, J. Chen, S. L. Schreiber, Chem. Biol. 1996, 3, 287-293; f) R. J. Kowalski, P. Giannakakou, S. P. Gunasekera, R. E. Longley, B. W. Day, E. Hamel, Mol. Pharmacol. 1997, 52, 613-622; isolation: g) S. P. Gunasekera, M. Gunasekera, R. E. Longley, G. K. Schulte, J. org. Chem. 1990, 55, 4912-4915.
147. Total synthesis: a) K. C. Nicolaou, F. van Delft, T. Ohshima, D. Vourloumis, J. Xu, S. Hosokawa, J. Pfefferkorn, S. Kim, T. Li, Angew. Chem. 1997, 109, 2631-2634; Angew. Chem. Int. Ed. Engl. 1997, 36, 2520-2524; isolation and biological activity: b) W. Fenical, P. R. Jensen, T. Lindel, US-A 5473057, 1995 [Chem. Abstr. 1996, 124, 194297z; c) T. Lindel, P. R. Jensen, W. Fenical, B. H. Long, A. M. Casazza, J. Carboni, C. R. Fairchild, J. Am. Chem. Soc. 1997, 119, 8744-8745.
148. Total synthesis: a) K. C. Nicolaou, F. van Delft, T. Ohshima, D. Vourloumis, J. Xu, S. Hosokawa, J. Pfefferkorn, S. Kim, T. Li, Angew. Chem. 1997, 109, 2631-2634; Angew. Chem. Int. Ed. Engl. 1997, 36, 2520-2524; isolation and biological activity: b) W. Fenical, P. R. Jensen, T. Lindel, US-A 5473057, 1995 [Chem. Abstr. 1996, 124, 194297z; c) T. Lindel, P. R. Jensen, W. Fenical, B. H. Long, A. M. Casazza, J. Carboni, C. R. Fairchild, J. Am. Chem. Soc. 1997, 119, 8744-8745.
149. Total synthesis: a) K. C. Nicolaou, F. van Delft, T. Ohshima, D. Vourloumis, J. Xu, S. Hosokawa, J. Pfefferkorn, S. Kim, T. Li, Angew. Chem. 1997, 109, 2631-2634; Angew. Chem. Int. Ed. Engl. 1997, 36, 2520-2524; isolation and biological activity: b) W. Fenical, P. R. Jensen, T. Lindel, US-A 5473057, 1995 [Chem. Abstr. 1996, 124, 194297z; c) T. Lindel, P. R. Jensen, W. Fenical, B. H. Long, A. M. Casazza, J. Carboni, C. R. Fairchild, J. Am. Chem. Soc. 1997, 119, 8744-8745.
150. Total synthesis: a) K. C. Nicolaou, F. van Delft, T. Ohshima, D. Vourloumis, J. Xu, S. Hosokawa, J. Pfefferkorn, S. Kim, T. Li, Angew. Chem. 1997, 109, 2631-2634; Angew. Chem. Int. Ed. Engl. 1997, 36, 2520-2524; isolation and biological activity: b) W. Fenical, P. R. Jensen, T. Lindel, US-A 5473057, 1995 [Chem. Abstr. 1996, 124, 194297z; c) T. Lindel, P. R. Jensen, W. Fenical, B. H. Long, A. M. Casazza, J. Carboni, C. R. Fairchild, J. Am. Chem. Soc. 1997, 119, 8744-8745.
151. Total synthesis: a) K. C. Nicolaou, J. Y. Xu, S. Kim, T. Ohshima, S. Hosokawa, J. Pfefferkorn, J. Am. Chem. Soc. 1997, 119, 11353-11354; isolation: b) M. D'Ambrosio, A. Guerriero, F. Pietra, Helv. Chim. Acta 1987, 70, 2019-2027; c) M. D'Ambrosio, A. Guerriero, F. Pietra, Helv. Chim. Acta 1988, 71, 964-976; biological activity: d) M. Ciomei, C. Albanese, W. Pastori, M. Grandi, F. Pietra, M. D'Ammbrosio, A. Guerriero, C. Battistini, Proc. Am. Assoc. Canc. Res. 1997, 38, 5.
152. Total synthesis: a) K. C. Nicolaou, J. Y. Xu, S. Kim, T. Ohshima, S. Hosokawa, J. Pfefferkorn, J. Am. Chem. Soc. 1997, 119, 11353-11354; isolation: b) M. D'Ambrosio, A. Guerriero, F. Pietra, Helv. Chim. Acta 1987, 70, 2019-2027; c) M. D'Ambrosio, A. Guerriero, F. Pietra, Helv. Chim. Acta 1988, 71, 964-976; biological activity: d) M. Ciomei, C. Albanese, W. Pastori, M. Grandi, F. Pietra, M. D'Ammbrosio, A. Guerriero, C. Battistini, Proc. Am. Assoc. Canc. Res. 1997, 38, 5.
153. Total synthesis: a) K. C. Nicolaou, J. Y. Xu, S. Kim, T. Ohshima, S. Hosokawa, J. Pfefferkorn, J. Am. Chem. Soc. 1997, 119, 11353-11354; isolation: b) M. D'Ambrosio, A. Guerriero, F. Pietra, Helv. Chim. Acta 1987, 70, 2019-2027; c) M. D'Ambrosio, A. Guerriero, F. Pietra, Helv. Chim. Acta 1988, 71, 964-976; biological activity: d) M. Ciomei, C. Albanese, W. Pastori, M. Grandi, F. Pietra, M. D'Ammbrosio, A. Guerriero, C. Battistini, Proc. Am. Assoc. Canc. Res. 1997, 38, 5.
154. Total synthesis: a) K. C. Nicolaou, J. Y. Xu, S. Kim, T. Ohshima, S. Hosokawa, J. Pfefferkorn, J. Am. Chem. Soc. 1997, 119, 11353-11354; isolation: b) M. D'Ambrosio, A. Guerriero, F. Pietra, Helv. Chim. Acta 1987, 70, 2019-2027; c) M. D'Ambrosio, A. Guerriero, F. Pietra, Helv. Chim. Acta 1988, 71, 964-976; biological activity: d) M. Ciomei, C. Albanese, W. Pastori, M. Grandi, F. Pietra, M. D'Ammbrosio, A. Guerriero, C. Battistini, Proc. Am. Assoc. Canc. Res. 1997, 38, 5.
155. L. Wessjohann, Angew. Chem. 1997, 109, 739-742; Angew. Chem. Int. Ed. Engl. 1997, 36, 715-718.
156. L. Wessjohann, Angew. Chem. 1997, 109, 739-742; Angew. Chem. Int. Ed. Engl. 1997, 36, 715-718.
157. M. Kalesse, Eur. Chem. Cron. 1997, 7-11.
158. M. R. V. Finlay, Chem. Ind. 1997, 24, 991-996.
159. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
160. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
161. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
162. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
163. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
164. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
165. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
166. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
167. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
168. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
169. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
170. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
171. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
172. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
173. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
174. For the development of the olefin metathesis as a ring forming reaction, see a) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452; b) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; c) P. R. Schwab, H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110; d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2055; e) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959; for some earlier pioneering studies on this reaction, see f) T. J. Katz, S. J. Lee, N. Acton, Tetrahedron Lett. 1976, 4247-4250; g) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 4241-4254; h) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; i) T. J. Katz, Adv. Organomet. Chem. 1977, 16, 283-317; for a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see j) A. Fürstner, K. Langemann, Synthesis 1997, 792-803; (k) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; (l) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; (m) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943-2944; (n) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; (o) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; (p) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
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