A multiply convergent platform for the synthesis of trioxacarcins

Proceedings of the National Academy of Sciences of the United States of America

Volumn 108, Issue 17, 2011, Pages 6709-6714

  Švenda, Jakub ^a   Hill, Nicholas ^a   Myers, Andrew G ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Anticancer; Chemical synthesis; DNA alkylation

Indexed keywords

DAUNORUBICIN; DC 45 A2; DOUBLE STRANDED DNA; NATURAL PRODUCT; NOGALAMYCIN; TRIOXACARCIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; DNA ALKYLATION; DRUG MECHANISM; DRUG STRUCTURE; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS;

ALKYLATION; AMINOGLYCOSIDES; ANTINEOPLASTIC AGENTS, ALKYLATING; DNA, NEOPLASM; HELA CELLS; HUMANS; MOLECULAR STRUCTURE;

EID: 79955566940     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1015257108     Document Type: Article

References (37)

1. Tomita F, Tamaoki T, Morimoto M, Fujimoto K (1981) Trioxacarcins, novel antitumor antibiotics I. Producing organism, fermentation and biological activities. J Antibiot 34:1519-1524. (Pubitemid 12104798)
2. Tamaoki T, Shirahata K, Iida T, Tomita F (1981) Trioxacarcins, novel antitumor antibiotics II. Isolation, physico-chemical properties and mode of action. J Antibiot 34:1525-1530. (Pubitemid 12104799)
3. Maiese WM, et al. (1990) LL-D49194 antibiotics, a novel family of antitumor agents: Taxonomy, fermentation and biological properties. J Antibiot 43:253-257.
4. Maskey RP, et al. (2004) Anti-cancer and antibacterial trioxacarcins with high antimalaria activity from a marine streptomycete and their absolute stereochemistry. J Antibiot 57:771-779. (Pubitemid 40143893)
5. Shirahata K, Iida T (1984) Compounds having antibiotic activity, processes for their preparation, pharmaceutical compositions containing them and their use as medicaments. US Patent 4,459,291.
6. Maskey RP, Sevvana M, Usón I, Helmke E, Laatsch H (2004) Gutingimycin: A highly complex metabolite from a marine streptomycete. Angew Chem Int Edit 43:1281-1283. (Pubitemid 39257952)
7. Fitzner A, Frauendorf H, Laatsch H, Diederichsen U (2008) Formation of gutingimycin: Analytical investigation of trioxacarcin A-mediated alkylation of dsDNA. Anal Bioanal Chem 390:1139-1147.
8. Pfoh R, Laatsch H, Sheldrick GM (2008) Crystal structure of trioxacarcin A covalently bound to DNA. Nucleic Acids Res 36:3508-3514. (Pubitemid 351859016)
9. Smith CK, Davies GJ, Dodson EJ, MooreMH (1995) DNA-nogalamycin interactions: The crystal structure of d(TGATCA) complexed with nogalamycin. Biochemistry 34:415-425.
10. Sun D, Hansen M, Clement JJ, Hurley LH (1993) Structure of the altromycin B (N7-guanine)- DNA adduct. A proposed prototypic DNA adduct structure for the pluramycin antitumor antibiotics. Biochemistry 32:8068-8074.
11. Tse WC, Boger DL (2004) Sequence-selective DNA recognition: Natural products and nature's lessons. Chem Biol 11:1607-1617. (Pubitemid 39651294)
12. Velluz L, Valls H, Nominé G (1965) Recent advances in the total synthesis of steroids. Angew Chem Int Edit 4:181-200.
13. Hendrickson JB (1977) Systematic synthesis design. 6. Yield analysis and convergency. J Am Chem Soc 99:5439-5450.
14. Evans DA, Bender SL, Morris J (1988) Total synthesis of the polyether antibiotic X-206. J Am Chem Soc 110:2506-2526.
15. Kaiser ET, et al. (1989) Peptide and protein synthesis by segment synthesis-condensation. Science 243:187-192. (Pubitemid 19035351)
16. Armstrong RW, et al. (1989) Total synthesis of a fully protected palytoxin carboxylic acid. J Am Chem Soc 111:7525-7530.
17. 1. Angew Chem Int Edit 33:858-62.
18. Nicolaou KC, et al. (1998) Total synthesis of brevetoxin A. Nature 392:264-269. (Pubitemid 28155095)
19. Smith AB, III, Kaufman MD, Beauchamp TJ, LaMarcheMJ, Arimoto H (1999) Gram-scale synthesis of (+)-discodermolide. Org Lett 1:1823-1826.
20. Warren JD, Miller JS, Keding SJ, Danishefsky SJ (2004) Towards fully synthetic glycoproteins by ultimately convergent routes: A solution to a long-standing problem. J Am Chem Soc 126:6576-6578. (Pubitemid 38697358)
21. Nielsen TE, Schreiber SL (2008) Towards the optimal screening collection: A synthesis strategy. Angew Chem Int Edit 47:48-56.
22. Charest MG, Lerner CD, Brubaker JD, Siegel DR, Myers AG (2005) A convergent enantioselective route to structurally diverse 6-deoxytetracycline antibiotics. Science 308:395-398. (Pubitemid 40530073)
23. Sun C, et al. (2008) A robust platform for the synthesis of new tetracycline antibiotics. J Am Chem Soc 130:17913-17927.
24. Huisgen R (1963) 1,3-Dipolar cycloadditions past and future. Angew Chem Int Edit 2:565-598.
25. Padwa A, Chinn RL, Hornbuckle SF, Zhi L (1989) Cyclic carbonyl ylide formation from the rhodium(II) acetate catalyzed reaction of 1-diazoalkanediones. Tetrahedron Lett 30:301-304.
26. Muthusamy S, et al. (2002) Tandem cyclization-cycloaddition behavior of rhodium carbenoids with carbonyl compounds: Stereoselective studies on the construction of novel epoxy-bridged tetrahydropyranone frameworks. J Org Chem 67:8019-8033. (Pubitemid 35331977)
27. Brzezinski LJ, Rafel S, Leahy JW (1997) The asymmetric Baylis-Hillman reaction. J Am Chem Soc 119:4317-4318. (Pubitemid 27239991)
28. Švenda J, Myers AG (2009) Anti-selective epoxidation of methyl α-methylene-β-tertbutyldimethylsilyloxycarboxylate esters. Evidence for stereospecific oxygen atom transfer in a nucleophilic epoxidation process. Org Lett 11:2437-2440.
29. de Silva SO, Reed JN, Snieckus V (1978) Directed lithiation of N,N-diethylbenzamides. Regiospecific synthesis of contiguously tri- and tetra-substituted alkoxybenzenes. Tetrahedron Lett 19:5099-5102.
30. Freskos JN, Morrow GW, Swenton JS (1985) Synthesis of functionalized hydroxyphthalides and their conversion to 3-cyano-1(3H)-isobenzofuranones. The Diels-Alder reaction of methyl 4,4-diethoxybutynoate and cyclohexadienes. J Org Chem 50:805-810.
31. Nomura K, Okazaki K, Hori K, Yoshii E (1986) Cyanophthalide annulation with 4-(5-alkoxy-2-furyl)-3-buten-2-one. Application to the synthesis of a (naphtho)pyrano- ã-lactone. Chem Pharm Bull 34:3175-3182.
32. Williams JM, et al. (1995) A new general method for preparation of N-methoxy-Nmethylamides. Application in direct conversion of an ester to a ketone. Tetrahedron Lett 36:5461-5464.
33. Brubaker JD, Myers AG (2007) A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics. Org Lett 9:3523-3525.
34. Kingsbury JS, Harrity JPA, Bonitatebus PJ, Hoveyda AH (1999) A recyclable Ru-based metathesis catalyst. J Am Chem Soc 121:791-799.
35. Kraus GA, Sugimoto H (1978) An annelation route to quinones. Tetrahedron Lett 19:2263-2266.
36. 4. Org Lett 6:3217-3219.
37. Trost BM, Caldwell CG (1981) The di-t-butylsilylene protecting group for diols. Tetrahedron Lett 22:4999-5002.