Synthesis of a bicyclobutane fatty acid identified from the cyanobacterium anabaena PCC 7120

Angewandte Chemie - International Edition

Volumn 50, Issue 42, 2011, Pages 9940-9942

  Deguire, Sean M ^a   Ma, Shutao ^b   Sulikowski, Gary A ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b SHANDONG UNIVERSITY   (China)

Author keywords

cascade reaction; cyclization; lipids; natural products; strained molecules

Indexed keywords

CASCADE REACTIONS; CYANOBACTERIUM ANABAENA; CYCLIZATION REACTIONS; NATURAL PRODUCTS; OXYLIPINS; STRAINED MOLECULES; TOTAL SYNTHESIS;

BUTANE; FATTY ACIDS; LIPIDS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

FATTY ACID;

ANABAENA; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANABAENA; FATTY ACIDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 80053898747     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201104366     Document Type: Article

References (25)

1. U. Jahn, J.-M. Galano, T. Durand, Angew. Chem. 2008, 120, 5978-6041
2. Angew. Chem. Int. Ed. 2008, 47, 5894-5955.
3. P. H. Buist, Nat. Prod. Rep. 2007, 24, 1110-1127.
4. A. Andreou, F. Brodhun, I. Feussner, Prog. Lipid Res. 2009, 48, 148-170.
5. M. Hamberg, H. Gardner, Biochim. Biophys. Acta Lipids Lipid Metab. 1993, 1165, 1-18.
6. A. Brash, S. Baertschi, C. Ingram, T. Harris, Proc. Natl. Acad. Sci. USA 1988, 85, 3382-3386.
7. C. Corre, G. L. Challis, Nat. Prod. Rep. 2009, 26, 977-986.
8. I. Feussner, C. Wasternack, Annu. Rev. Plant Biol. 2002, 53, 275-297.
9. C. Schneider, K. Niisuke, W. E. Boeglin, M. Voehler, D. F. Stec, N. A. Porter, A. R. Brash, Proc. Natl. Acad. Sci. USA 2007, 104, 18941-18945.
10. W. Gerwick, Lipids 1996, 31, 1215-1231.
11. W. Gerwick, Chem. Rev. 1993, 93, 1807-1823.
12. A. de Meijere, S. I. Kozhushkov, H. Schill, Chem. Rev. 2006, 106, 4926-4996.
13. L. Tietze, Chem. Rev. 1996, 96, 115-136.
14. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344
15. Angew. Chem. Int. Ed. 2006, 45, 7134-7186.
16. T. Bentley, B. Engels, T. Hupp, E. Bogdan, M. Christl, J. Org. Chem. 2006, 71, 1018-1026.
17. W. Bailey, Y. Tao, Tetrahedron Lett. 1997, 38, 6157-6158.
18. K. Miura, Y. Ichinose, K. Nozaki, K. Fugami, K. Oshima, K. Utimoto, Bull. Chem. Soc. Jpn. 1989, 62, 143-145.
19. K. Sadhu, D. Matteson, Tetrahedron Lett. 1986, 27, 795-798.
20. I. Delamarche, P. Mossett, J. Org. Chem. 1994, 59, 5453-5457.
21. J-;L. Luche, J. Am. Chem. Soc. 1978, 100, 2226-2227.
22. A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.
23. R. W. Murray, Chem. Rev. 1989, 89, 1187-1201.
24. O. Mitsunobu, Synthesis 1981, 1-28.
25. J. S. Sinninghe Damsté, M. Strous, W. I. C. Rijpstra, E. C. Hopmans, J. A. J. Geenevasen, A. C. T. van Duin, L. A. van Niftrik, M. S. M. Jetten, Nature 2002, 419, 708-712.