Biogenetically-inspired total synthesis of epidithiodiketopiperazines and related alkaloids

Accounts of Chemical Research

Volumn 48, Issue 4, 2015, Pages 1159-1171

  Kim, Justin ^a   Movassaghi, Mohammad ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; EPIDITHIODIKETOPIPERAZINE; PIPERAZINE DERIVATIVE;

CELL PROLIFERATION; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG EFFECTS; HELA CELL LINE; HUMAN; MCF 7 CELL LINE; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ALKALOIDS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; HELA CELLS; HUMANS; MCF-7 CELLS; MOLECULAR CONFORMATION; PIPERAZINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84928324336     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar500454v     Document Type: Article

References (47)

1. Hauser, D. et al. Helv. Chim. Acta 1970, 53, 1061
2. Katagiri, K. et al. J. Antibiot. 1970, 23, 420
3. Greiner, D. et al. Nat. Chem. Biol. 2005, 1, 143
4. Jiang, C.-S.; Guo, Y.-W. Mini-Rev. Med. Chem. 2011, 11, 728
5. Hauser, D.; Weber, H. P.; Sigg, H. P. Isolierung und Strukturaufklärung von Chaetocin Helv. Chim. Acta 1970, 53, 1061-1073
6. Katagiri, K.; Sato, K.; Hayakawa, S.; Matsushima, T.; Minato, H. Verticillin A, A New Antibiotic from Verticillium sp J. Antibiot. 1970, 23, 420-422
7. Jiang, C.-S.; Guo, Y.-W. Epipolythiodioxopiperazines from Fungi: Chemistry and Bioactivities Mini-Rev. Med. Chem. 2011, 11, 728-745
8. Kim, J.; Ashenhurst, J. A.; Movassaghi, M. Total Synthesis of (+)-11,11′Dideoxyverticillin A Science 2009, 324, 238-241
9. Kim, J.; Movassaghi, M. Biogenetically Inspired Syntheses of Alkaloid Natural Products Chem. Soc. Rev. 2009, 38, 3035-3050
10. Movassaghi, M.; Siegel, D. S.; Han, S. Total Synthesis of All (-)-Agelastatin Alkaloids Chem. Sci. 2010, 1, 561-566
11. Han, S.; Movassaghi, M. Concise Total Synthesis and Stereochemical Revision of all (-)-Trigonoliimines J. Am. Chem. Soc. 2011, 133, 10768-10771
12. Johnson, W. S.; Semmelhack, M. F.; Sultanbawa, M. U. S.; Dolak, L. A. A New Approach to Steroid Total Synthesis. A Nonenzymic Biogenetic-Like Olefinic Cyclization Involving the Stereospecific Formation of Five Asymmetric Centers J. Am. Chem. Soc. 1968, 90, 2994-2996
13. Kirby, G. W.; Robins, D. J. The Biosynthesis of Gliotoxin and Related Epipolythiodioxopiperazines. In The Biosynthesis of Mycotoxins; Steyn, P. S., Ed.; Academic Press: New York, 1980; pp 301-326.
14. Taylor, A. The Toxicology of Sporidesmins and Other Epipolythiadioxopiperazines. In Microbial Toxins; Kadis, S.; Ciegler, A.; Ajl, S. J., Eds.; Academic Press: New York, 1971; Vol. 7, pp 337-376.
15. Sammes, P. G. Naturally Occurring 2,5-Dioxopiperazines and Related Compounds. In Progress in the Chemistry of Organic Natural Products; Zechmeister, L.; Herz, W.; Grisebach, H.; Kirby, G. W., Eds.; Springer: Vienna, Austria, 1975; Vol. 32, pp 51-118.
16. Gardiner, D. M.; Waring, P.; Howlett, B. J. The Epipolythiodioxopiperazine (ETP) Class of Fungal Toxins: Distribution, Mode of Action, Functions and Biosynthesis Microbiology 2005, 151, 1021-1032
17. Gardiner, D. M.; Howlett, B. J. Bioinformatic and Expression Analysis of the Putative Gliotoxin Biosynthetic Gene Cluster of Aspergillus fumigatus FEMS Microbiol. Lett. 2005, 248, 241-248
18. Fox, E. M.; Howlett, B. J. Biosynthetic Gene Clusters for Epipolythiodioxopiperazines in Filamentous Fungi Mycol. Res. 2008, 112, 162-169
19. Fukuyama, T.; Nakatsuka, S.-I.; Kishi, Y. Total Synthesis of Gliotoxin, Dehydrogliotoxin and Hyalodendrin Tetrahedron 1981, 37, 2045-2078
20. Poisel, H.; Schmidt, U. Syntheseversuche in der Reihe der 3.6-Epidithio-2.5-dioxo-piperazin-Antibiotika Gliotoxin, Sporidesmin, Aranotin und Chaetocin, II Chem. Ber. 1971, 104, 1714-1721
21. Williams, R. M.; Rastetter, W. H. Syntheses of the Fungal Metabolites (±)-Gliovictin and (±)-Hyalodendrin J. Org. Chem. 1980, 45, 2625-2631
22. Miller, S. J. Total Chemical Synthesis Peers into the Biosynthetic Black Box Science 2009, 324, 186-187
23. Movassaghi, M.; Schmidt, M. A. Concise Total Synthesis of (-)-Calycanthine, (+)-Chimonanthine, and (+)-Folicanthine Angew. Chem., Int. Ed. 2007, 46, 3725-3728
24. Woodward, R. B.; Yang, N. C.; Katz, T. J.; Clark, V. M.; Harley-Mason, J.; Ingleby, R. F.; Shepard, N. Calycanthine: The Structure of the Alkaloid and Its Degradation Product, Calycanine Proc. Chem. Soc., London 1960, 76-78
25. Robinson, R.; Teuber, H. J. Reactions with Nitrosodisulfonate. IV. Calycanthine and Calycanthidine Chem. Ind. 1954, 783-784
26. Schmidt, M. A.; Movassaghi, M. New Strategies for the Synthesis of Hexahydropyrroloindole Alkaloids Inspired by Biosynthetic Hypotheses Synlett 2008, 313-324
27. Movassaghi, M.; Schmidt, M. A.; Ashenhurst, J. A. Concise Total Synthesis of (+)-WIN 64821 and (-)-Ditryptophenaline Angew. Chem., Int. Ed. 2008, 47, 1485-1487
28. Movassaghi, M.; Ahmad, O. K.; Lathrop, S. P. Directed Heterodimerization: Stereocontrolled Assembly via Solvent-Caged Unsymmetrical Diazene Fragmentation J. Am. Chem. Soc. 2011, 133, 13002-13005
29. Lathrop, S. P.; Movassaghi, M. Application of Diazene-Directed Fragment Assembly to the Total Synthesis and Stereochemical Assignment of (+)-Desmethyl-meso-chimonanthine and Related Heterodimeric Alkaloids Chem. Sci. 2014, 5, 333-340
30. Lathrop, S. P.; Kim, J.; Movassaghi, M. Radical Mediated Dimerization and Oxidation Reactions for the Synthesis of Complex Alkaloids Chimia 2012, 66, 389-393
31. Raju, R.; Piggott, A. M.; Conte, M.; Aalbersberg, W. G. L.; Feussner, K.; Capon, R. J. Naseseazines A and B: A New Dimeric Diketopiperazine Framework from a Marine-Derived Actinomycete, Streptomyces sp Org. Lett. 2009, 11, 3862-3865
32. Kim, J.; Movassaghi, M. Concise Total Synthesis and Stereochemical Revision of (+)-Naseseazines A and B: Regioselective Arylative Dimerization of Diketopiperazine Alkaloids J. Am. Chem. Soc. 2011, 133, 14940-14943
33. Lee, S.; MacMillan, D. W. C. Organocatalytic Vinyl and Friedel-Crafts Alkylations with Trifluoroborate Salts J. Am. Chem. Soc. 2007, 129, 15438-15439
34. Molander, G. A.; Ellis, N. Organotrifluoroborates: Protected Boronic Acids That Expand the Versatility of the Suzuki Coupling Reaction Acc. Chem. Res. 2007, 40, 275-286
35. Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. Conversion of Arylboronic Acids into Potassium Aryltrifluoroborates: Convenient Precursors of Arylboron Difluoride Lewis Acids J. Org. Chem. 1995, 60, 3020-3027
36. Boyer, N.; Movassaghi, M. Concise Total Synthesis of (+)-Gliocladins B and C Chem. Sci. 2012, 3, 1798-1803
37. Coste, A.; Kim, J.; Adams, T. C.; Movassaghi, M. Concise Total Synthesis of (+)-Bionectins A and C Chem. Sci. 2013, 4, 3191-3197
38. Herscheid, J. D. M.; Nivard, R. J. F.; Tijhuis, M. W.; Scholten, H. P. H.; Ottenheijm, H. C. J. α-Functionalized Amino Acid Derivatives. A Synthetic Approach of Possible Biogenetic Importance J. Org. Chem. 1980, 45, 1880-1885
39. Kim, J.; Movassaghi, M. General Approach to Epipolythiodiketopiperazine Alkaloids: Total Synthesis of (+)-Chaetocins A and C and (+)-12,12′Dideoxychetracin A J. Am. Chem. Soc. 2010, 132, 14376-14378
40. Scharf, D. H.; Remme, N.; Habel, A.; Chankhamjon, P.; Scherlach, K.; Heinekamp, T.; Hortschansky, P.; Brakhage, A. A.; Hertweck, C. A Dedicated Glutathione S-Transferase Mediates Carbon-Sulfur Bond Formation in Gliotoxin Biosynthesis J. Am. Chem. Soc. 2011, 133, 12322-12325
41. Scharf, D. H.; Habel, A.; Heinekamp, T.; Brakhage, A. A.; Hertweck, C. Opposed Effects of Enzymatic Gliotoxin N- and S-Methylations J. Am. Chem. Soc. 2014, 136, 11674-11679
42. Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. Alkylation of Amino Acids without Loss of the Optical Activity: Preparation of α-Substituted Proline Derivatives. A Case of Self-Reproduction of Chirality J. Am. Chem. Soc. 1983, 105, 5390-5398
43. Iwasa, E.; Hamashima, Y.; Fujishiro, S.; Higuchi, E.; Ito, A.; Yoshida, M.; Sodeoka, M. Total Synthesis of (+)-Chaetocin and Its Analogues: Their Histone Methyltransferase G9a Inhibitory Activity J. Am. Chem. Soc. 2010, 132, 4078-4079
44. Scharf, D. H.; Chankhamjon, P.; Scherlach, K.; Heinekamp, T.; Roth, M.; Brakhage, A. A.; Hertweck, C. Epidithiol Formation by an Unprecedented Twin Carbon-Sulfur Lyase in the Gliotoxin Pathway Angew. Chem., Int. Ed. 2012, 51, 10064-10068
45. Scharf, D. H.; Chankhamjon, P.; Scherlach, K.; Heinekamp, T.; Willing, K.; Brakhage, A. A.; Hertweck, C. Epidithiodiketopiperazine Biosynthesis: A Four-Enzyme Cascade Converts Glutathione Conjugates into Transannular Disulfide Bridges Angew. Chem., Int. Ed. 2013, 52, 11092-11095
46. Davis, C.; Carberry, S.; Schrettl, M.; Singh, I.; Stephens, J. C.; Barry, S. M.; Kavanagh, K.; Challis, G. L.; Brougham, D.; Doyle, S. The Role of Glutathione S-Transferase GliG in Gliotoxin Biosynthesis in Aspergillus fumigatus Chem. Biol. 2011, 18, 542-552
47. Boyer, N.; Morrison, K. C.; Kim, J.; Hergenrother, P. J.; Movassaghi, M. Synthesis and Anticancer Activity of Epipolythiodiketopiperazine Alkaloids Chem. Sci. 2013, 4, 1646-1657