Investigations into the manzamine alkaloid biosynthetic hypothesis

Angewandte Chemie - International Edition

Volumn 37, Issue 19, 1998, Pages 2661-2663

  Baldwin, Jack E ^a   Claridge, Timothy D W ^a   Culshaw, Andrew J ^a   Heupel, Florian A ^a   Lee, Victor ^a   Spring, David R ^a   Whitehead, Roger C ^a   Boughtflower, Robert J ^b   Mutton, Ian M ^b   Upton, Richard J ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Alkaloids; Biomimetic synthesis; Biosynthesis; Diels Alder reactions; Manzamine

Indexed keywords

EID: 0032538363     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981016)37:19<2661::AID-ANIE2661>3.0.CO;2-D     Document Type: Article

References (30)

1. D. J. Faulkner, Nat. Prod. Rep. 1997, 14, 259-302, and references therein; C. A. Bewley and D. J. Faulkner, Angew. Chem. 1998, 110, 2280-2297; Angew. Chem. Int. Ed. 1998, 37, 2162-2178.
2. D. J. Faulkner, Nat. Prod. Rep. 1997, 14, 259-302, and references therein; C. A. Bewley and D. J. Faulkner, Angew. Chem. 1998, 110, 2280-2297; Angew. Chem. Int. Ed. 1998, 37, 2162-2178.
3. D. J. Faulkner, Nat. Prod. Rep. 1997, 14, 259-302, and references therein; C. A. Bewley and D. J. Faulkner, Angew. Chem. 1998, 110, 2280-2297; Angew. Chem. Int. Ed. 1998, 37, 2162-2178.
4. M. J. Garson, Nat. Prod. Rep. 1989, 6, 143-170.
5. R. Sakai, T. Higa, C. W. Jefford, G. Bernardinelli, J. Am. Chem. Soc. 1986, 108, 6404-6405.
6. R. Sakai, S. Kohmoto, T. Higa, C. W. Jefford, G. Bernardinelli, Tetrahedron Lett. 1987, 28, 5493-5496.
7. J. E. Baldwin, R. C. Whitehead, Tetrahedron Lett. 1992, 33, 2059-2062.
8. For previous model studies, see a) J. E. Baldwin, T. D. W. Claridge, F. A. Heupel, R. C. Whitehead, Tatrahedron Lett. 1994, 35, 7829-7832; b) L. Gil, A. Gateau-Olesker, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 707-710; c) L. Gil, A. Gateau-Olesker, Y.-S. Wong, L. Chernatova, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 2059-2062; d) L. Gil, X. Baucherel, M.-T. Martin, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 6231-6234; e) J. E. Baldwin, T. D. W. Claridge, A. J. Culshaw, F. A. Heupel, S. Smrcková, R. C. Whitehead, Tetrahedron Lett. 1996, 37, 6919-6922; f) J. E. Baldwin, L. Bischoff, T. D. W. Claridge, F. A. Heupel, D. R. Spring, R. C. Whitehead, Tetrahedron 1997, 53, 2271-2290.
9. For previous model studies, see a) J. E. Baldwin, T. D. W. Claridge, F. A. Heupel, R. C. Whitehead, Tatrahedron Lett. 1994, 35, 7829-7832; b) L. Gil, A. Gateau-Olesker, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 707-710; c) L. Gil, A. Gateau-Olesker, Y.-S. Wong, L. Chernatova, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 2059-2062; d) L. Gil, X. Baucherel, M.-T. Martin, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 6231-6234; e) J. E. Baldwin, T. D. W. Claridge, A. J. Culshaw, F. A. Heupel, S. Smrcková, R. C. Whitehead, Tetrahedron Lett. 1996, 37, 6919-6922; f) J. E. Baldwin, L. Bischoff, T. D. W. Claridge, F. A. Heupel, D. R. Spring, R. C. Whitehead, Tetrahedron 1997, 53, 2271-2290.
10. For previous model studies, see a) J. E. Baldwin, T. D. W. Claridge, F. A. Heupel, R. C. Whitehead, Tatrahedron Lett. 1994, 35, 7829-7832; b) L. Gil, A. Gateau-Olesker, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 707-710; c) L. Gil, A. Gateau-Olesker, Y.-S. Wong, L. Chernatova, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 2059-2062; d) L. Gil, X. Baucherel, M.-T. Martin, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 6231-6234; e) J. E. Baldwin, T. D. W. Claridge, A. J. Culshaw, F. A. Heupel, S. Smrcková, R. C. Whitehead, Tetrahedron Lett. 1996, 37, 6919-6922; f) J. E. Baldwin, L. Bischoff, T. D. W. Claridge, F. A. Heupel, D. R. Spring, R. C. Whitehead, Tetrahedron 1997, 53, 2271-2290.
11. For previous model studies, see a) J. E. Baldwin, T. D. W. Claridge, F. A. Heupel, R. C. Whitehead, Tatrahedron Lett. 1994, 35, 7829-7832; b) L. Gil, A. Gateau-Olesker, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 707-710; c) L. Gil, A. Gateau-Olesker, Y.-S. Wong, L. Chernatova, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 2059-2062; d) L. Gil, X. Baucherel, M.-T. Martin, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 6231-6234; e) J. E. Baldwin, T. D. W. Claridge, A. J. Culshaw, F. A. Heupel, S. Smrcková, R. C. Whitehead, Tetrahedron Lett. 1996, 37, 6919-6922; f) J. E. Baldwin, L. Bischoff, T. D. W. Claridge, F. A. Heupel, D. R. Spring, R. C. Whitehead, Tetrahedron 1997, 53, 2271-2290.
12. For previous model studies, see a) J. E. Baldwin, T. D. W. Claridge, F. A. Heupel, R. C. Whitehead, Tatrahedron Lett. 1994, 35, 7829-7832; b) L. Gil, A. Gateau-Olesker, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 707-710; c) L. Gil, A. Gateau-Olesker, Y.-S. Wong, L. Chernatova, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 2059-2062; d) L. Gil, X. Baucherel, M.-T. Martin, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 6231-6234; e) J. E. Baldwin, T. D. W. Claridge, A. J. Culshaw, F. A. Heupel, S. Smrcková, R. C. Whitehead, Tetrahedron Lett. 1996, 37, 6919-6922; f) J. E. Baldwin, L. Bischoff, T. D. W. Claridge, F. A. Heupel, D. R. Spring, R. C. Whitehead, Tetrahedron 1997, 53, 2271-2290.
13. For previous model studies, see a) J. E. Baldwin, T. D. W. Claridge, F. A. Heupel, R. C. Whitehead, Tatrahedron Lett. 1994, 35, 7829-7832; b) L. Gil, A. Gateau-Olesker, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 707-710; c) L. Gil, A. Gateau-Olesker, Y.-S. Wong, L. Chernatova, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 2059-2062; d) L. Gil, X. Baucherel, M.-T. Martin, C. Marazano, B. C. Das, Tetrahedron Lett. 1995, 36, 6231-6234; e) J. E. Baldwin, T. D. W. Claridge, A. J. Culshaw, F. A. Heupel, S. Smrcková, R. C. Whitehead, Tetrahedron Lett. 1996, 37, 6919-6922; f) J. E. Baldwin, L. Bischoff, T. D. W. Claridge, F. A. Heupel, D. R. Spring, R. C. Whitehead, Tetrahedron 1997, 53, 2271-2290.
14. S. Laschat, Angew. Chem. 1996, 108, 313-315; Angew. Chem. Int. Ed. Engl. 1996, 35, 289-291.
15. S. Laschat, Angew. Chem. 1996, 108, 313-315; Angew. Chem. Int. Ed. Engl. 1996, 35, 289-291.
16. Reviews: a) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 302-352; b) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794; c) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prop. Proced. Int. 1998, 30, 1-51; more recent examples: d) J. Kobayashi, D. Watanabe, N. Kawasaki, M. Tsuda, J. Org. Chem. 1997, 62, 9236-9239; e) Y. Guo, E. Trivellone, G. Scognamiglio, G. Cimino, Tetrahedron 1998, 54, 541-550; f) F. Kong, E. I. Graziani, R. J. Andersen, J. Nat. Prod. 1998, 61, 267-271; g) M. Tsuda, D. Watanabe, J. Kobayashi, Tetrahedron Lett. 1998, 39, 1207-1210; h) D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692; i) R. J. Clark, K. L. Field, R. D. Charan, M. J. Gibson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826; for a recent review on the total synthesis of manzamine alkaloids see: j) E. Magnier, Y. Langlois, Tetrahedron 1998, 54, 6201-6258.
17. Reviews: a) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 302-352; b) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794; c) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prop. Proced. Int. 1998, 30, 1-51; more recent examples: d) J. Kobayashi, D. Watanabe, N. Kawasaki, M. Tsuda, J. Org. Chem. 1997, 62, 9236-9239; e) Y. Guo, E. Trivellone, G. Scognamiglio, G. Cimino, Tetrahedron 1998, 54, 541-550; f) F. Kong, E. I. Graziani, R. J. Andersen, J. Nat. Prod. 1998, 61, 267-271; g) M. Tsuda, D. Watanabe, J. Kobayashi, Tetrahedron Lett. 1998, 39, 1207-1210; h) D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692; i) R. J. Clark, K. L. Field, R. D. Charan, M. J. Gibson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826; for a recent review on the total synthesis of manzamine alkaloids see: j) E. Magnier, Y. Langlois, Tetrahedron 1998, 54, 6201-6258.
18. Reviews: a) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 302-352; b) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794; c) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prop. Proced. Int. 1998, 30, 1-51; more recent examples: d) J. Kobayashi, D. Watanabe, N. Kawasaki, M. Tsuda, J. Org. Chem. 1997, 62, 9236-9239; e) Y. Guo, E. Trivellone, G. Scognamiglio, G. Cimino, Tetrahedron 1998, 54, 541-550; f) F. Kong, E. I. Graziani, R. J. Andersen, J. Nat. Prod. 1998, 61, 267-271; g) M. Tsuda, D. Watanabe, J. Kobayashi, Tetrahedron Lett. 1998, 39, 1207-1210; h) D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692; i) R. J. Clark, K. L. Field, R. D. Charan, M. J. Gibson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826; for a recent review on the total synthesis of manzamine alkaloids see: j) E. Magnier, Y. Langlois, Tetrahedron 1998, 54, 6201-6258.
19. Reviews: a) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 302-352; b) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794; c) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prop. Proced. Int. 1998, 30, 1-51; more recent examples: d) J. Kobayashi, D. Watanabe, N. Kawasaki, M. Tsuda, J. Org. Chem. 1997, 62, 9236-9239; e) Y. Guo, E. Trivellone, G. Scognamiglio, G. Cimino, Tetrahedron 1998, 54, 541-550; f) F. Kong, E. I. Graziani, R. J. Andersen, J. Nat. Prod. 1998, 61, 267-271; g) M. Tsuda, D. Watanabe, J. Kobayashi, Tetrahedron Lett. 1998, 39, 1207-1210; h) D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692; i) R. J. Clark, K. L. Field, R. D. Charan, M. J. Gibson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826; for a recent review on the total synthesis of manzamine alkaloids see: j) E. Magnier, Y. Langlois, Tetrahedron 1998, 54, 6201-6258.
20. Reviews: a) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 302-352; b) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794; c) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prop. Proced. Int. 1998, 30, 1-51; more recent examples: d) J. Kobayashi, D. Watanabe, N. Kawasaki, M. Tsuda, J. Org. Chem. 1997, 62, 9236-9239; e) Y. Guo, E. Trivellone, G. Scognamiglio, G. Cimino, Tetrahedron 1998, 54, 541-550; f) F. Kong, E. I. Graziani, R. J. Andersen, J. Nat. Prod. 1998, 61, 267-271; g) M. Tsuda, D. Watanabe, J. Kobayashi, Tetrahedron Lett. 1998, 39, 1207-1210; h) D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692; i) R. J. Clark, K. L. Field, R. D. Charan, M. J. Gibson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826; for a recent review on the total synthesis of manzamine alkaloids see: j) E. Magnier, Y. Langlois, Tetrahedron 1998, 54, 6201-6258.
21. Reviews: a) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 302-352; b) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794; c) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prop. Proced. Int. 1998, 30, 1-51; more recent examples: d) J. Kobayashi, D. Watanabe, N. Kawasaki, M. Tsuda, J. Org. Chem. 1997, 62, 9236-9239; e) Y. Guo, E. Trivellone, G. Scognamiglio, G. Cimino, Tetrahedron 1998, 54, 541-550; f) F. Kong, E. I. Graziani, R. J. Andersen, J. Nat. Prod. 1998, 61, 267-271; g) M. Tsuda, D. Watanabe, J. Kobayashi, Tetrahedron Lett. 1998, 39, 1207-1210; h) D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692; i) R. J. Clark, K. L. Field, R. D. Charan, M. J. Gibson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826; for a recent review on the total synthesis of manzamine alkaloids see: j) E. Magnier, Y. Langlois, Tetrahedron 1998, 54, 6201-6258.
22. Reviews: a) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 302-352; b) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794; c) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prop. Proced. Int. 1998, 30, 1-51; more recent examples: d) J. Kobayashi, D. Watanabe, N. Kawasaki, M. Tsuda, J. Org. Chem. 1997, 62, 9236-9239; e) Y. Guo, E. Trivellone, G. Scognamiglio, G. Cimino, Tetrahedron 1998, 54, 541-550; f) F. Kong, E. I. Graziani, R. J. Andersen, J. Nat. Prod. 1998, 61, 267-271; g) M. Tsuda, D. Watanabe, J. Kobayashi, Tetrahedron Lett. 1998, 39, 1207-1210; h) D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692; i) R. J. Clark, K. L. Field, R. D. Charan, M. J. Gibson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826; for a recent review on the total synthesis of manzamine alkaloids see: j) E. Magnier, Y. Langlois, Tetrahedron 1998, 54, 6201-6258.
23. Reviews: a) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 302-352; b) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794; c) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prop. Proced. Int. 1998, 30, 1-51; more recent examples: d) J. Kobayashi, D. Watanabe, N. Kawasaki, M. Tsuda, J. Org. Chem. 1997, 62, 9236-9239; e) Y. Guo, E. Trivellone, G. Scognamiglio, G. Cimino, Tetrahedron 1998, 54, 541-550; f) F. Kong, E. I. Graziani, R. J. Andersen, J. Nat. Prod. 1998, 61, 267-271; g) M. Tsuda, D. Watanabe, J. Kobayashi, Tetrahedron Lett. 1998, 39, 1207-1210; h) D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692; i) R. J. Clark, K. L. Field, R. D. Charan, M. J. Gibson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826; for a recent review on the total synthesis of manzamine alkaloids see: j) E. Magnier, Y. Langlois, Tetrahedron 1998, 54, 6201-6258.
24. Reviews: a) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 302-352; b) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794; c) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prop. Proced. Int. 1998, 30, 1-51; more recent examples: d) J. Kobayashi, D. Watanabe, N. Kawasaki, M. Tsuda, J. Org. Chem. 1997, 62, 9236-9239; e) Y. Guo, E. Trivellone, G. Scognamiglio, G. Cimino, Tetrahedron 1998, 54, 541-550; f) F. Kong, E. I. Graziani, R. J. Andersen, J. Nat. Prod. 1998, 61, 267-271; g) M. Tsuda, D. Watanabe, J. Kobayashi, Tetrahedron Lett. 1998, 39, 1207-1210; h) D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692; i) R. J. Clark, K. L. Field, R. D. Charan, M. J. Gibson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826; for a recent review on the total synthesis of manzamine alkaloids see: j) E. Magnier, Y. Langlois, Tetrahedron 1998, 54, 6201-6258.
25. Reviews: a) R. J. Andersen, R. W. M. Van Soest, F. Kong in Alkaloids: Chemical and Biological Perspectives, Vol. 10 (Ed.: S. W. Pelliter), Pergamon, London, 1996, pp. 302-352; b) M. Tsuda, J. Kobayashi, Heterocycles 1997, 46, 765-794; c) N. Matzanke, R. J. Gregg, S. M. Weinreb, Org. Prop. Proced. Int. 1998, 30, 1-51; more recent examples: d) J. Kobayashi, D. Watanabe, N. Kawasaki, M. Tsuda, J. Org. Chem. 1997, 62, 9236-9239; e) Y. Guo, E. Trivellone, G. Scognamiglio, G. Cimino, Tetrahedron 1998, 54, 541-550; f) F. Kong, E. I. Graziani, R. J. Andersen, J. Nat. Prod. 1998, 61, 267-271; g) M. Tsuda, D. Watanabe, J. Kobayashi, Tetrahedron Lett. 1998, 39, 1207-1210; h) D. Watanabe, M. Tsuda, J. Kobayashi, J. Nat. Prod. 1998, 61, 689-692; i) R. J. Clark, K. L. Field, R. D. Charan, M. J. Gibson, I. M. Brereton, A. C. Willis, Tetrahedron 1998, 54, 8811-8826; for a recent review on the total synthesis of manzamine alkaloids see: j) E. Magnier, Y. Langlois, Tetrahedron 1998, 54, 6201-6258.
26. a) J. Kobayashi, M. Tsuda, N. Kawasaki, K. Matsumoto, T. Adachi, Tetrahedron Lett. 1994, 35, 4383-4386;
27. b) F. Kong, R. J. Andersen, Tetrahedron 1995, 51, 2895-2906.
28. +): 381.3270.
29. 4, all the signals arising from 7 had virtually disappeared. Therefore, the majority of 13 was not derived from the reduction of 7.
30. J. D. Winkler, J. M. Axten, J. Am. Chem. Soc. 1998, 120, 6425-6426.