Chemistry and biology of roseophilin and the prodigiosin alkaloids: A survey of the last 2500 years

Angewandte Chemie - International Edition

Volumn 42, Issue 31, 2003, Pages 3582-3603

  Fürstner, Alois ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Alkaloids; Heterocycles; Immunosuppression; Natural products; Total synthesis

Indexed keywords

BLOOD; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL);

CYTOTOXIC AGENTS;

HYDROCARBONS;

ALKALOID DERIVATIVE; CYCLOSPORIN A; NATURAL PRODUCT; PNU 156804; PRODIGIOSIN; ROSEOPHILIN; TAMBJAMINE; TSUKUBAENOLIDE; UNCLASSIFIED DRUG;

CYTOTOXICITY; DRUG ACTIVITY; DRUG DETERMINATION; DRUG IDENTIFICATION; DRUG POTENTIATION; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; HUMAN; NONHUMAN; REVIEW; RING CLOSING METATHESIS; SCIENCE; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; ANIMALS; ANTI-INFECTIVE AGENTS; HETEROCYCLIC COMPOUNDS, 3-RING; HISTORY, 16TH CENTURY; HISTORY, 19TH CENTURY; HISTORY, 20TH CENTURY; HISTORY, ANCIENT; HISTORY, MEDIEVAL; HUMANS; MOLECULAR STRUCTURE; PRODIGIOSIN; PYRROLES;

EID: 17744417463     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200300582     Document Type: Review

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119. Note, however, that there remains same ambiguity in this regard as long as the function of five genes in the red cluster is unknown.
120. Streptomyces coelicolor produces a mixture of 2 and 4 as the main biochromes in a ratio of about 2:1; see: S.-W. Tsao, B. A. M. Rudd, X.-G. He, C.-J. Chang, H. G. Floss, J. Antibiot. 1985, 38, 128-131.
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129. For further syntheses of non-natural prodigiosin analogues by similar condensation reactions, see reference [9] and the following: a) W. R. Hearn, M. K. Elson, R. H. Williams, J. Medina-Castro, J. Org. Chem. 1970, 35, 142-146;
130. b) A. J. Blake, G. A. Hunter, H. McNab, J. Chem. Soc. Chem. Commun. 1990, 734-736;
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137. 2-catalyzed skeletal reorganizations developed by other groups, see: a) N. Chatani, N. Furukawa, H. Sakurai, S. Mural, Organometallics 1996, 15, 901-903; b) N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105; c) M. Méndez, M.P. Muñoz, C. Nevado, D.J. Cárdenas, A.M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520; d) C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222; e) B. Martín-Matute, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2001, 113, 4890-4893; Angew. Chem. Int. Ed. 2001, 40, 4754-4757; f) S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709; g) J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569; h) B. M. Trost, V. K. Chang, Synthesis 1993, 824-832.
138. 2-catalyzed skeletal reorganizations developed by other groups, see: a) N. Chatani, N. Furukawa, H. Sakurai, S. Mural, Organometallics 1996, 15, 901-903; b) N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105; c) M. Méndez, M.P. Muñoz, C. Nevado, D.J. Cárdenas, A.M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520; d) C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222; e) B. Martín-Matute, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2001, 113, 4890-4893; Angew. Chem. Int. Ed. 2001, 40, 4754-4757; f) S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709; g) J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569; h) B. M. Trost, V. K. Chang, Synthesis 1993, 824-832.
139. 2-catalyzed skeletal reorganizations developed by other groups, see: a) N. Chatani, N. Furukawa, H. Sakurai, S. Mural, Organometallics 1996, 15, 901-903; b) N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105; c) M. Méndez, M.P. Muñoz, C. Nevado, D.J. Cárdenas, A.M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520; d) C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222; e) B. Martín-Matute, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2001, 113, 4890-4893; Angew. Chem. Int. Ed. 2001, 40, 4754-4757; f) S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709; g) J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569; h) B. M. Trost, V. K. Chang, Synthesis 1993, 824-832.
140. 2-catalyzed skeletal reorganizations developed by other groups, see: a) N. Chatani, N. Furukawa, H. Sakurai, S. Mural, Organometallics 1996, 15, 901-903; b) N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105; c) M. Méndez, M.P. Muñoz, C. Nevado, D.J. Cárdenas, A.M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520; d) C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222; e) B. Martín-Matute, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2001, 113, 4890-4893; Angew. Chem. Int. Ed. 2001, 40, 4754-4757; f) S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709; g) J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569; h) B. M. Trost, V. K. Chang, Synthesis 1993, 824-832.
141. 2-catalyzed skeletal reorganizations developed by other groups, see: a) N. Chatani, N. Furukawa, H. Sakurai, S. Mural, Organometallics 1996, 15, 901-903; b) N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105; c) M. Méndez, M.P. Muñoz, C. Nevado, D.J. Cárdenas, A.M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520; d) C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222; e) B. Martín-Matute, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2001, 113, 4890-4893; Angew. Chem. Int. Ed. 2001, 40, 4754-4757; f) S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709; g) J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569; h) B. M. Trost, V. K. Chang, Synthesis 1993, 824-832.
142. 2-catalyzed skeletal reorganizations developed by other groups, see: a) N. Chatani, N. Furukawa, H. Sakurai, S. Mural, Organometallics 1996, 15, 901-903; b) N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105; c) M. Méndez, M.P. Muñoz, C. Nevado, D.J. Cárdenas, A.M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520; d) C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222; e) B. Martín-Matute, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2001, 113, 4890-4893; Angew. Chem. Int. Ed. 2001, 40, 4754-4757; f) S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709; g) J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569; h) B. M. Trost, V. K. Chang, Synthesis 1993, 824-832.
143. 2-catalyzed skeletal reorganizations developed by other groups, see: a) N. Chatani, N. Furukawa, H. Sakurai, S. Mural, Organometallics 1996, 15, 901-903; b) N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105; c) M. Méndez, M.P. Muñoz, C. Nevado, D.J. Cárdenas, A.M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520; d) C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222; e) B. Martín-Matute, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2001, 113, 4890-4893; Angew. Chem. Int. Ed. 2001, 40, 4754-4757; f) S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709; g) J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569; h) B. M. Trost, V. K. Chang, Synthesis 1993, 824-832.
144. 2-catalyzed skeletal reorganizations developed by other groups, see: a) N. Chatani, N. Furukawa, H. Sakurai, S. Mural, Organometallics 1996, 15, 901-903; b) N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105; c) M. Méndez, M.P. Muñoz, C. Nevado, D.J. Cárdenas, A.M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520; d) C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222; e) B. Martín-Matute, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2001, 113, 4890-4893; Angew. Chem. Int. Ed. 2001, 40, 4754-4757; f) S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709; g) J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569; h) B. M. Trost, V. K. Chang, Synthesis 1993, 824-832.
145. 2-catalyzed skeletal reorganizations developed by other groups, see: a) N. Chatani, N. Furukawa, H. Sakurai, S. Mural, Organometallics 1996, 15, 901-903; b) N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105; c) M. Méndez, M.P. Muñoz, C. Nevado, D.J. Cárdenas, A.M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520; d) C. Fernández-Rivas, M. Méndez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222; e) B. Martín-Matute, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2001, 113, 4890-4893; Angew. Chem. Int. Ed. 2001, 40, 4754-4757; f) S. Oi, I. Tsukamoto, S. Miyano, Y. Inoue, Organometallics 2001, 20, 3704-3709; g) J. Blum, H. Beer-Kraft, Y. Badrieh, J. Org. Chem. 1995, 60, 5567-5569; h) B. M. Trost, V. K. Chang, Synthesis 1993, 824-832.
146. B. M. Trost, G. A. Doherty, J. Am. Chem. Soc. 2000, 122, 3801-3810.
147. R. D'Allessio, A. Rossi, Synlett 1996, 513-514.
148. Catalyst 78 is a readily available substitute for the classical Grubbs catalyst; for a large-scale adaptable preparation and a survey of its reactivity, see: A. Fürstner, O. Guth, A. Düffels, G. Seidel, M. Liebl, B. Gabor, R. Mynott, Chem. Eur. J. 2001, 7, 4811-4820.
149. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
150. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
151. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
152. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
153. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
154. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
155. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
156. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
157. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
158. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
159. For previous applications of this catalyst in synthesis, see references [39,55] and the following: a) A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602; b) A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742; c) A. Fürstner, K. Radkowski, Chem. Commun. 2001, 671-672; d) A. Fürstner, F. Jeanjean, P. Razon, Angew. Chem. 2002, 114, 2203-2206; Angew. Chem. Int. Ed. 2002, 41, 2097-2101; e) A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C. W. Lehmann, R. Mynott, J. Am. Chem. Soc. 2002, 124, 7061-7069; f) A. Fürstner, M. Schlede, Adv. Synth. Catal. 2002, 344, 657-665; g) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871; h) A. Fürstner, F. Jeanjean, P. Razon, C. Wirtz, R. Mynott, Chem. Eur. J. 2003, 9, 320-326; i) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
160. a) A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1998, 120, 2817-2825;
161. b) A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1997, 119, 2944-2945.
162. a) P. E. Harrington, M. A. Tius, J. Am. Chem. Soc. 2001, 123, 8509-8514;
163. b) P. E. Harrington, M. A. Tius, Org. Lett. 1999, 1, 649-651.
164. D. L. Boger, J. Hong, J. Am. Chem. Soc. 2001, 123, 8515-8519.
165. S. H. Kim, I. Figueroa, P. L. Fuchs, Tetrahedron Lett. 1997, 38, 2601-2604.
166. A. Fürstner, T. Gastner, H. Weintritt, J. Org. Chem. 1999, 64, 2361-2366.
167. a) S. J. Bamford, T. Luker, W. N. Speckamp, H. Hiemstra, Org. Lett. 2000, 2, 1157-1160;
168. b) see also: S. J. Bamford, K. Goubitz, H. L. van Lingen, T. Luker, H. Schenk, H. Hiemstra, J. Chem. Soc. Perkin Trans. 1 2000, 345-351.
169. B. M. Trost, G. A. Doherty, J. Am. Chem. Soc. 2000, 122, 3801-3810.
170. T. Mochizuki, E. Itoh, N. Shibata, S. Nakatani, T. Katoh, S. Terashima, Tetrahedron Lett. 1998, 39, 6911-6914.
171. a) J. Robertson, R. J. D. Hatley, D. J. Watkin, J. Chem. Soc. Perkin Trans. 1 2000, 3389-3396;
172. b) J. Robertson, R.J.D. Hatley, Chem. Commun. 1999, 1455-1456.
173. For model studies, see: a) S. H. Kim, Z. Jin, P. L. Fuchs, Tetrahedron Lett. 1995, 36, 4537-4538; b) S.H. Kim, P. L. Fuchs, Tetrahedron Lett. 1996, 37, 2545-2548; c) M. A. Fagan, D. W Knight, Tetrahedron Lett. 1999, 40, 6117-6120; d) T. Luker, W.-J. Koot, H. Hiemstra, W. N. Speckamp, J. Org. Chem. 1998, 63, 220-221.
174. For model studies, see: a) S. H. Kim, Z. Jin, P. L. Fuchs, Tetrahedron Lett. 1995, 36, 4537-4538; b) S.H. Kim, P. L. Fuchs, Tetrahedron Lett. 1996, 37, 2545-2548; c) M. A. Fagan, D. W Knight, Tetrahedron Lett. 1999, 40, 6117-6120; d) T. Luker, W.-J. Koot, H. Hiemstra, W. N. Speckamp, J. Org. Chem. 1998, 63, 220-221.
175. For model studies, see: a) S. H. Kim, Z. Jin, P. L. Fuchs, Tetrahedron Lett. 1995, 36, 4537-4538; b) S.H. Kim, P. L. Fuchs, Tetrahedron Lett. 1996, 37, 2545-2548; c) M. A. Fagan, D. W. Knight, Tetrahedron Lett. 1999, 40, 6117-6120; d) T. Luker, W.-J. Koot, H. Hiemstra, W. N. Speckamp, J. Org. Chem. 1998, 63, 220-221.
176. For model studies, see: a) S. H. Kim, Z. Jin, P. L. Fuchs, Tetrahedron Lett. 1995, 36, 4537-4538; b) S.H. Kim, P. L. Fuchs, Tetrahedron Lett. 1996, 37, 2545-2548; c) M. A. Fagan, D. W Knight, Tetrahedron Lett. 1999, 40, 6117-6120; d) T. Luker, W.-J. Koot, H. Hiemstra, W. N. Speckamp, J. Org. Chem. 1998, 63, 220-221.
177. For further studies concerning the heteroaromatic segment 81 and its analogues, see reference [74] and the following: a) S. Nakatani, M. Kirihara, K. Yamada, S. Terashima, Tetrahedron Lett. 1995, 36, 8461-8464; b) J. Robertson, N. Kuhnert, Y. Zhao, Heterocycles 2000, 53, 2415-2420.
178. For further studies concerning the heteroaromatic segment 81 and its analogues, see reference [74] and the following: a) S. Nakatani, M. Kirihara, K. Yamada, S. Terashima, Tetrahedron Lett. 1995, 36, 8461-8464; b) J. Robertson, N. Kuhnert, Y. Zhao, Heterocycles 2000, 53, 2415-2420.
179. a) A. Fürstner, T. Gastner, J. Rust, Synlett 1999, 29-32;
180. b) A. Fürstner, T. Gastner, Org. Lett. 2000, 2, 2467-2470.
181. For selected reviews, see: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29;
182. b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172;
183. Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
184. c) R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450;
185. d) M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144;
186. Angew. Chem. Int. Ed. Engl. 1997, 36, 2037-2056;
187. e) A. Fürstner, Top. Catal. 1997, 4, 285-299;
188. f) S. K. Armstrong, J. Chem. Soc. Perkin Trans. 1 1998, 371-388.
189. a) P. Schwab, M. B. France, J. W. Ziller, R. H. Grubbs, Angew. Chem. 1995, 107, 2179-2181;
190. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039-2041;
191. b) S. T. Nguyen, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1993, 115, 9858, 9859.
192. H. Falk, The Chemistry of Linear Oligopyrroles and Bile Pigments, Springer, Berlin, 1989.
193. For further studies from our laboratory and pertinent literature on other bioactive pyrrole alkaloids, see the following references and literature cited therein: a) A. Fürstner, H. Weintritt, A. Hupperts, J. Org. Chem. 1995, 60, 6637-6641; b) A. Fürstner, H. Krause, O. R. Thiel, Tetrahedron 2002, 58, 6373-6380; c) A. Fürstner, A. Hupperts, A. Ptock, E. Janssen, J. Org. Chem. 1994, 59, 5215-5229.
194. For further studies from our laboratory and pertinent literature on other bioactive pyrrole alkaloids, see the following references and literature cited therein: a) A. Fürstner, H. Weintritt, A. Hupperts, J. Org. Chem. 1995, 60, 6637-6641; b) A. Fürstner, H. Krause, O. R. Thiel, Tetrahedron 2002, 58, 6373-6380; c) A. Fürstner, A. Hupperts, A. Ptock, E. Janssen, J. Org. Chem. 1994, 59, 5215-5229.
195. For further studies from our laboratory and pertinent literature on other bioactive pyrrole alkaloids, see the following references and literature cited therein: a) A. Fürstner, H. Weintritt, A. Hupperts, J. Org. Chem. 1995, 60, 6637-6641; b) A. Fürstner, H. Krause, O. R. Thiel, Tetrahedron 2002, 58, 6373-6380; c) A. Fürstner, A. Hupperts, A. Ptock, E. Janssen, J. Org. Chem. 1994, 59, 5215-5229.
196. For more authoritative treatises of this and related aspects, see: a) E. J. Corey, X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989; b) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122; K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis: Targets, Strategies, Methods, Wiley-VCH, Weinheim, 1996, and references therein.
197. For more authoritative treatises of this and related aspects, see: a) E. J. Corey, X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989; b) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122; K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis: Targets, Strategies, Methods, Wiley-VCH, Weinheim, 1996, and references therein.
198. For more authoritative treatises of this and related aspects, see: a) E. J. Corey, X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989; b) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122; K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis: Targets, Strategies, Methods, Wiley-VCH, Weinheim, 1996, and references therein.
199. For more authoritative treatises of this and related aspects, see: a) E. J. Corey, X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989; b) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122; K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis: Targets, Strategies, Methods, Wiley-VCH, Weinheim, 1996, and references therein.