Total syntheses of (-)-transtaganolide A, (+)-transtaganolide B, (+)-transtaganolide C, and (-)-transtaganolide D and biosynthetic implications

Angewandte Chemie - International Edition

Volumn 52, Issue 26, 2013, Pages 6699-6703

  Nelson, Hosea M ^a   Gordon, Jonny R ^a   Virgil, Scott C ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

biomimetic synthesis; biosynthesis; cycloaddition; rearrangement; total synthesis

Indexed keywords

ABSOLUTE CONFIGURATION; BIOMIMETIC SYNTHESIS; CASCADE REACTIONS; DIASTEREOSELECTIVE; ENANTIOSELECTIVE TOTAL SYNTHESIS; REARRANGEMENT; TOTAL SYNTHESIS; X-RAY DIFFRACTION DATA;

BIOCHEMISTRY; BIOMIMETIC PROCESSES; CYCLOADDITION; X RAY DIFFRACTION;

BIOSYNTHESIS;

ARTEMISININ DERIVATIVE; BASILIOLIDE B; PLANT EXTRACT; PYRONE DERIVATIVE; SESQUITERPENE; THAPSIGARGIN; TRANSTAGANOLIDE C; TRANSTAGANOLIDE D;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; METABOLISM; SYNTHESIS; TEMPERATURE; THAPSIA;

ARTEMISININS; DRUG DESIGN; MOLECULAR STRUCTURE; PLANT EXTRACTS; PYRONES; SESQUITERPENES; TEMPERATURE; THAPSIA; THAPSIGARGIN;

EID: 84879362744     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201301212     Document Type: Article

References (25)

1. S. B. Christensen, U. Rasmussen, Tetrahedron Lett. 1980, 21, 3829-3830
2. S. B. Christensen, A. Andersen, U. W. Smitt, Prog. Chem. Org. Nat. Prod. 1997, 71, 130-167.
3. J. Lytton, M. Westlin, M. R. Hanley, J. Biol. Chem. 1991, 266, 17067-17071.
4. A. Saouf, F. M. Guerra, J. J. Rubal, F. J. Moreno-Dorado, M. Akssira, F. Mellouki, M. Lopez, A. J. Pujadas, Z. D. Jorge, G. M. Massanet, Org. Lett. 2005, 7, 881-884
5. G. Appendino, S. Prosperini, C. Valdivia, M. Ballero, G. Colombano, R. A. Billington, A. A. Genazzani, O. Sterner, J. Nat. Prod. 2005, 68, 1213-1217.
6. C. Navarrete, R. Sancho, F. J. Caballero, F. Pollastro, B. L. Fiebich, O. Sterner, G. Appendino, E. Munoz, J. Pharmacol. Exp. Ther. 2006, 319, 422-430.
7. H. M. Nelson, K. Murakami, S. C. Virgil, B. M. Stoltz, Angew. Chem. 2011, 123, 3772-3775
8. Angew. Chem. Int. Ed. 2011, 50, 3688-3691.
9. H. M. Nelson, B. M. Stoltz, Tetrahedron Lett. 2009, 50, 1699-1701
10. R. Larsson, O. Sterner, M. Johansson, Org. Lett. 2009, 11, 657-660.
11. J. J. Rubal, F. J. Moreno-Dorado, F. M. Guerra, D. J. Zacarias, S. Abderrahmane, A. Mohamed, M. Fouad, R. G. Raul, G. M. Massanet, Phytochemistry 2007, 68, 2480-2486.
12. E. J. Corey, D. H. Lee, J. Am. Chem. Soc. 1991, 113, 4026-4028
13. U. Kazmayer, A. Krebs, Angew. Chem. 1995, 107, 2213-2214
14. Angew. Chem. Int. Ed. Engl. 1995, 34, 2012-2014.
15. R. E. Ireland, M. D. Varney, J. Am. Chem. Soc. 1984, 106, 3668-3670.
16. W. Zeng, R. Fröhlich, D. Hoppe, Tetrahedron 2005, 61, 3281-3287
17. S. A. Snyder, D. S. Treitler, Angew. Chem. 2009, 121, 8039-8043
18. Angew. Chem. Int. Ed. 2009, 48, 7899-7903.
19. E. Fillion, R. L. Beingessner, J. Org. Chem. 2003, 68, 9485-9488.
20. W. C. Still, C. Gennari, Tetrahedron Lett. 1983, 24, 4405-4408.
21. J. M. Batista, S. N. Lõpez, J. Da Silva Mota, K. L. Vanzolini, Q. B. Cass, D. Rinaldo, W. Vilegas, V. Da Silva Bolzani, M. J. Kato, M. Furlan, Chirality 2009, 21, 799-801.
22. M. V. Kozytska, G. B. Dudley, Tetrahedron Lett. 2008, 49, 2899-2901.
23. R. E. Ireland, P. Wipf, J. N. Xiang, J. Org. Chem. 1991, 56, 3572-3582
24. S. Gül, F. Schoenebeck, V. Aviyente, K. N. Houk, J. Org. Chem. 2010, 75, 2115-2118.
25. Comparison of CD spectra to the bulk material confirmed that the mounted crystal represented the major enantiomer in the 89.5 % ee bulk. CCDC 937177 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.