Enantioselective total synthesis of some brevicomins using aldolase antibody 38C2

Chemistry - A European Journal

Volumn 4, Issue 5, 1998, Pages 881-885

  List, Benjamin ^a   Shabat, Doron ^a   Barbas III, Carlos F ^a   Lerner, Richard A ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Aldol reactions; Antibody catalysis; Brevicomin; Enantioselective catalysis; Total synthesis

Indexed keywords

EID: 0031779141     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19980515)4:5<881::aid-chem881>3.0.co;2-%23     Document Type: Article

References (24)

1. a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley-Interscience, 1994;
2. b) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, 1993.
3. For recent examples of catalytic enantioselective aldol reactions, see: a) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942-1944; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873;
4. For recent examples of catalytic enantioselective aldol reactions, see: a) Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942-1944; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873;
5. b) E. M. Carreira, W. Lee, R. A. Singer, J. Am. Chem. Soc. 1995, 117, 3649-3650, and references therein.
6. J. Wagner, R. A. Lerner, C. F. Barbas III, Science 1995, 270, 1797.
7. C. F Barbas III, A. Heine, G. Zhong, T. Hoffmann, S. Gramatikova, R. Bjoernstedt, B. List, J. Anderson, E. Stura, A., I. A. Wilson, R. A. Lerner, Science 1997, 278, 2085-2092.
8. T. Huffman, G. Zhong, B. List, D. Shabat, J. Anderson, S. Gramatikova, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 1998, in press.
9. G. Zhong, T Hoffmann, R. A. Lerner, S. Danishefsky, C. F. Barbas III, J. Am. Chem. Soc. 1997, 119, 8131-8132.
10. S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1995, 117, 3653-3654.
11. R. M. Silverstein, R. G. Brownlee, T. E. Bellas, D. L. Wood, L. E. Browne, Science, 1968, 159, 889.
12. J. H. Borden, in Comprehensive Insect Physiology Biochemistry and Pharmacology, Vol. 9 (Eds.: G. A. Kerkut, L. I. Gilber), Pergamon Press, New York, 1985, 257-285.
13. a) G. D. Prestwich, Pure Appl. Chem. 1989, 61, 551-554;
14. b) W. Francke, F. Schroeder, P. Philipp, H. Meyer, V. Shinnwell, G. Gries, Bioorg. Med. Chem. 1996, 4, 363-374;
15. c) H. Takikawa, K.-i. Shimbo, K. Mori, Liebigs Ann. 1997, 821-824;
16. d) Y. Yokoyama, K. Mori, ibid. 1997, 845-849.
17. exo-Brevicomin (1) has been synthesized by using an aldolase enzyme (rabbit muscle aldolase). However, this natural aldolase is restricted to dihydroxyacetone phosphate as the donor. This limitation requires the subsequent enzymatic removal of the phosphate group. M. Schultz, H. Waldmann, W. Vogt, H. Kunz, Tetrahedron Lett. 1990, 31, 867-868.
18. G. F. Zhong, D. Shabat, B. List, J. Andereson, S. C. Sinha, R. A. Lerner, C. F. Barbas III, unpublished results.
19. Aldehyde 7 was prepared in two steps from commercial 5-oxohexanenitril.
20. J. Mulzer, B.List, Tetrahedron Lett. 1994, 35, 9021-9024.
21. P. J. Walsh, K. B. Sharpless, Synlett 1993, 605-606.
22. Aldehyde 10 was prepared in two steps from commercial ethyl levulinate.
23. T. Taniguchi, H. Ohnishi, K. Ogasawara, Chem. Commun. 1996, 1477-1478.
24. J. Mulzer, H. J. Martin, B. List, Tetrahedron. Lett. 1996, 9177-9178.