An eight-step synthesis of epicolactone reveals its biosynthetic origin

Nature Chemistry

Volumn 7, Issue 11, 2015, Pages 879-882

  Ellerbrock, Pascal ^a   Armanino, Nicolas ^a   Ilg, Marina K ^a   Webster, Robert ^a   Trauner, Dirk ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE;

CHEMISTRY; CYCLOADDITION; SYNTHESIS;

CYCLOADDITION REACTION; LACTONES;

EID: 84945115676     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2336     Document Type: Article

References (28)

1. Nicolaou, K. C., Vourloumis, D., Winssinger, N. &Baran, P. S. The art and science of total synthesis at the dawn of the twenty-first century. Angew. Chem. Int. Ed. 39, 44-122 (2000)
2. Nicolaou, K. C. &Sorensen, E. J. Classics in Total Synthesis (VCH, 1996)
3. Nicolaou, K. C. &Snyder, S. A. Classics in Total Synthesis II (Wiley-VCH, 2003)
4. Corey, E. J. Retrosynthetic thinking-essentials and examples. Chem. Soc. Rev. 17, 111-133 (1988)
5. Corey, E. J. &Cheng, X. M. The Logic of Chemical Synthesis (Wiley, 1995)
6. Corey, E. J. Nobel Lecture. The logic of chemical synthesis: multistep synthesis of complex carbogenic molecules. (1990); www.nobelprize.org/nobel-prizes/chemistry/laureates/1990/coreylecture.html
7. Wilson, R. M. &Danishefsky, S. J. Pattern recognition in retrosynthetic analysis: snapshots in total synthesis. J. Org. Chem. 72, 4293-4305 (2007)
8. Bishop, C. M. Pattern Recognition and Machine Learning (Springer, 2006)
9. da Silva Araujo, F. D. et al. Epicolactone-natural product isolated from the sugarcane endophytic fungus Epicoccum nigrum. Eur. J. Org. Chem. 2012, 5225-5230 (2012)
10. Talontsi, F. M., Dittrich, B., Schuffler, A., Sun, H. &Laatsch, H. Epicoccolides: antimicrobial and antifungal polyketides from an endophytic fungus Epicoccum sp. associated with Theobroma cacao. Eur. J. Org. Chem. 2013, 3174-3180 (2013)
11. Bruckl, T., Baxter, R. D., Ishihara, Y. &Baran, P. S. Innate and guided C-H functionalization logic. Acc. Chem. Res. 45, 826-839 (2012)
12. Barltrop, J. A. &Nicholson, J. S. The oxidation products of phenols. Part I. The structure of purpurogallin. J. Chem. Soc. 1948, 116-120 (1948)
13. Matsuo, Y., Tanaka, T. &Kouno, I. A new mechanism for oxidation of epigallocatechin and production of benzotropolone pigments. Tetrahedron 62, 4774-4783 (2006)
14. Bentley, R. A fresh look at natural tropolonoids. Nat. Prod. Rep. 25, 118-138 (2008)
15. Armstrong, S. M. &Patel, T. R. Microbial degradation of phloroglucinol and other polyphenolic compounds. J. Basic Microbiol. 34, 123-135 (1994)
16. Durckheimer, W. &Paulus, E. F. Mechanism of purpurogallin formation: an adduct from 3-hydroxy-o-benzoquinone and 4, 5-dimethyl-o-benzoquinone. Angew. Chem. Int. Ed. Engl. 24, 224-225 (1985)
17. Kemami Wangun, H. V., Ishida, K. &Hertweck, C. Epicoccalone, a coumarintype chymotrypsin inhibitor, and isobenzofuran congeners from an Epicoccum sp. associated with a tree fungus. Eur. J. Org. Chem. 2008, 3781-3784 (2008)
18. Ishikawa, Y., Ito, T. &Lee, K. H. Inhibition of sardine flesh lipoxygenase by a new antioxidant from Aspergillus terreus. J. Jpn Oil Chem. Soc. 45, 1321-1325 (1996)
19. Cook, S. P. &Danishefsky, S. J. An interesting issue of Diels-Alder selectivity discovered en route to 11-O-debenzoyltashironin. Org. Lett. 8, 5693-5695 (2006)
20. Ellerbrock, P., Armanino, N. &Trauner, D. Biomimetic synthesis of the calcineurin phosphatase inhibitor dibefurin. Angew. Chem. Int. Ed. 53, 13414-13418 (2014)
21. Strych, S. et al. Biomimetic total synthesis of santalin Y. Angew. Chem. Int. Ed. 54, 5079-5083 (2015)
22. Sofiyev, V., Lumb, J.-P., Volgraf, M. &Trauner, D. Total synthesis of exiguamines A and B inspired by catecholamine chemistry. Chem. Eur. J. 18, 4999-5005 (2012)
23. Brown, P. D., Willis, A. C., Sherburn, M. S. &Lawrence, A. L. Total synthesis of incarviditone and incarvilleatone. Org. Lett. 14, 4537-4539 (2012)
24. Gravel, E. &Poupon, E. Biogenesis and biomimetic chemistry: can complex natural products be assembled spontaneously? Eur. J. Org. Chem. 2008, 27-42 (2008)
25. Poupon, E. &Nay, B. Biomimetic Organic Synthesis (Wiley-VCH, 2011)
26. Razzak, M. &De Brabander, J. K. Lessons and revelations from biomimetic syntheses. Nature Chem. Biol. 7, 865-875 (2011)
27. Tietze, L. F., Brasche, G. &Gericke, K. M. Domino Reactions in Organic Synthesis (Wiley-VCH, 2006)
28. Willstatter, R. &Heiss, H. Uber die Konstitution des Purpurogallins. Liebigs Ann. Chem. 433, 17-33 (1923)