Synthesis of a functionalized oxabicyclo[2.2.1]-heptene-based chemical library

Combinatorial Chemistry and High Throughput Screening

Volumn 15, Issue 1, 2012, Pages 81-89

  Luesse, Sarah B ^a,b   Wells, Gregg ^a,b   Miller, Jeanne ^c   Bolstad, Erin ^a,b   Bergmeier, Stephen C ^c   McMills, Mark C ^a,b   Priestley, Nigel D ^a,b   Wright, Dennis L ^a,b  

^a Promiliad Biopharma   (United States)

^b Promiliad Biopharma   (United States)

^c OHIO UNIVERSITY   (United States)

Author keywords

Acetal; Antibacterial; Oxabicyclo 2.2.1 heptene

Indexed keywords

BICYCLO COMPOUND; OXABICYCLO[2.2.1]HEPTENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACILLUS SUBTILIS; BICYCLO COMPOUNDS; CANDIDA GLABRATA; HEPTANES; MICROBIAL SENSITIVITY TESTS; SMALL MOLECULE LIBRARIES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84863293700     PISSN: 13862073     EISSN: 18755402     Source Type: Journal    
DOI: 10.2174/138620712798280835     Document Type: Article

References (31)

1. Luesse, S.B.; Wells, G.; Nayek, A.; Smith, A.E.; Kusche, B.R.; Bergmeier, S.C.; McMills, M.C.; Priestley, N.D.; Wright, D.L. Natural products in parallel synthesis: Triazole libraries of nonactic acid. Bioorg. Med. Chem. Lett., 2008, 18(14), 3946-3949.
2. Schindler, C.S.; Carreira, E.M. Rapid formation of complexity in the total synthesis of natural products enabled by oxabicyclo[2.2.1]heptene building blocks. Chem. Soc. Rev., 2009, 38(11), 3222-3241.
3. Eggelte, T.A.; Koning, H.D.; Huisman, H.O. Synthesis of 9,11-epoxy-9a-homoprostaglandin analogues. J. Chem. Soc., Perkin Trans. 1, 1978, (9), 980-989.
4. Das, J.; Vu, T.; Harris, D.N.; Ogletree, M.L. Synthesis and pharmacological evaluation of 5,6-exo-epoxy-7-oxabicyclo[2.2.1]heptane derivatives. J. Med. Chem., 1988, 31(5), 930-935.
5. Sprague, P.W.; Heikes, J.E.; Gougoutas, J.Z.; Malley, M.F.; Harris, D.N.; Greenberg, R. Synthesis and in vitro pharmacology of 7-oxabicyclo[2.2.1]heptane analogs of thromboxane A2/PGH2. J. Med. Chem., 1985, 28(11), 1580-1590.
6. Zhou, H.B.; Comninos, J.S.; Stossi, F.; Katzenellenbogen, B.S.; Katzenellenbogen, J.A. Synthesis and evaluation of estrogen receptor ligands with bridged oxabicyclic cores containing a diarylethylene motif: Estrogen antagonists of unusual structure. J. Med. Chem., 2005, 48(23), 7261-7274. (Pubitemid 41748144)
7. Hart, M.E.; Chamberlin, A.R.; Walkom, C.; Sakoff. J.A.; McCluskey, A. Modified norcantharidins. Bioorg. Med. Chem. Lett., 2004, 14(8), 1969-1973.
8. Hill, T.A.; Stewart, S.G.; Ackland, S.P.; Gilbert, J.; Sauer, B.; Sakoff, J.A.; McCluskey, A. Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation. Bioorg. Med. Chem. Lett., 2007, 15(18), 6126-6134. (Pubitemid 47088962)
9. Hill, T.A.; Stewart, S.G.; Sauer, B.; Gilbert, J.; Ackland, S.P.; Sakoff, J.A.; McCluskey, A. Heterocyclic substituted cantharidin and norcantharidin analogues-synthesis, protein phosphatase (1 and 2A) inhibition, and anti-cancer activity. Bioorg. Med. Chem. Lett., 2007, 17(12), 3392-3397. (Pubitemid 46819022)
10. McCluskey, A.; Ackland, S.P.; Bowyer, M.C.; Baldwin, M.L.; Garner, J.; Walkom, C.C.; Sakoff, J.A. Cantharidin analogues: Synthesis and evaluation of growth inhibition in a panel of selected tumour cell lines. Bioorg. Chem., 2003, 31(1), 68-79. (Pubitemid 36411927)
11. McCluskey, A.; Sim, A.T.R.; Sakoff, J.A. Serine-Threonine protein phosphatase inhibitors: Development of potential therapeutic strategies. J. Med. Chem., 2002, 45(6), 1151-1175. (Pubitemid 34263552)
12. Baba, Y.; Hirukawa, N.; Tanohira, N.; Sodeoka, M. Structure-Based Design of a Highly Selective Catalytic Site-Directed Inhibitor of Ser/Thr Protein Phosphatase 2B (Calcineurin). J. Am. Chem. Soc., 2003, 125(32), 9740-9749. (Pubitemid 36975936)
13. Bailey, T.R.; Rippin, S.R.; Opsitnick, E.; Burns, C.J.; Pevear, D.C.; Collett, M.S.; Rhodes, G.; Tohan, S.; Huggins, J.W.; Baker, R.O.; Kern, E.R.; Keith, K.A.; Dai, D.; Yang, G.; Hruby, D.; Jordan, R. N-(3,3a,4,4a,5,5a,6,6a- Octahydro-1,3-dioxo-4,6- ethenocycloprop[f]isoindol-2-(1H)-yl)carboxamides: Identification of Novel Orthopoxvirus Egress Inhibitors. J. Med. Chem., 2007, 50(7), 1442-1444.
14. Still, W.C.; Kahn, M.; Mitra, A. Rapid Chromatographic Technique for Preparative separations with moderate resolution. J. Org. Chem., 1978, 43(14), 2923-2925.
15. Caruana, P.A.; Frontier, A.J. Dearomatization of furans via [2,3]-Still-Wittig rearrangement. Tetrahedron, 2004, 60(48), 10921-10926. (Pubitemid 40292277)
16. Davey, K.G.; Szekely, A.; Johnson, E.M.; Warnock, D.W. Comparison of a new commercial colorimetric microdilution method with a standard method for in-vitro susceptibility testing of Candida spp. and Cryptococcus neoformans. J. Antibiotic Chemother., 1998, 42(4), 439-444. (Pubitemid 28473002)
17. CLSI. (2008) Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. M07-A8. CLSI.
18. Fujioka, H.; Fujita, T.; Kotoku, N.; Ohba, Y.; Nagatomi, Y.; Hiramatsu A.; Kita, Y. Asymmetric desymmetrization based on an intramolecular haloetherification: A highly effective and recyclable chiral nonracemic auxiliary, 2-exo-Methyl-3-endo-phenyl-5-norbornene-2-carboxaldehyde, for meso-1,3- and meso-1,4-Diols. Chem. Eur. J., 2004, 10(21), 5386-5397.
19. Benningshof, J.C.J.; Blaauw, R.H.; van Ginkel, A.E.; van Maarseveen, J.H.; Rutjes, F.P.J.T.; Hiemstra, H. Studies towards the total synthesis of solanoeclepin A: synthesis of the 7-oxabicyclo[2.2.1]heptane moiety and attempted seven-membered ring formation. J. Chem. Soc., Perkin Trans. 1, 2002, (14), 1693-1700.
20. Benningshof, J.C.J.; IJsselstijn, M.; Wallner, S.R.; Koster, A.L.; Blaauw, R.H.; van Ginkel, A.E.; Brière, J.-F.; van Maarseveen, J.H.; Rutjes, F.P.J.T.; Hiemstra, H. Studies towards the total synthesis of solanoeclepin A: synthesis and potato cyst nematode hatching activity of analogues containing the tetracyclic left-hand substructure. J. Chem. Soc., Perkin Trans. 1, 2002, (14), 1701-1713.
21. Yuan, K.; Zhang, T.K.; Hou, X.L. A Highly Efficient Palladacycle Catalyst for Hydrophenylation of C-, N-, and O-Substituted Bicyclic Alkenes under Aerobic Condition. J. Org. Chem., 2005, 70(15), 6085-6088. (Pubitemid 40995350)
22. Larock, R.C.; Johnson, P.L. Palladium-catalysed intermolecular arylation and alkenylation of bicylic alkenes. J. Chem. Soc., Chem. Commun., 1989, (18), 1368.
23. Li, X.-G.; Tang, F.-Y.; Xu, H.-D.; Wu, X.-Y.; Zhou, Q.-L. Asymmetric hydroarylation of hetero-atom containing norbornene derivatives and enantioselective synthesis of analogs of epibatidine Arkivoc, 2003, ii(ii), 15-20.
24. Ponten, F.; Magnusson, G. Synthesis of polycyclic oxanorbornanes via a sequential epoxyhexopyranoside ring contraction-intramolecular diels-alder reaction. J. Org. Chem., 1997, 62(23), 7978-7983. (Pubitemid 127494460)
25. Zhang, W.; Wang, L.X.; Shi, W.J.; Zhou, Q.L. Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with grignard reagents. J. Org. Chem., 2005, 70(9), 3734-3736.
26. Arrayas, R.G.; Cabrera, S.; Carretero, J.C. Copper-catalyzed antistereo-controlled ring opening of oxabicyclic alkenes with grignard reagents. Org. Lett., 2003, 5(8), 1333-1336. (Pubitemid 37162076)
27. Lautens, M.; Ma, S. Nickel-catalyzed addition of grignard reagents to oxabicyclic compounds. Ring-opening reactions with previously unreactive substrates and nucleophiles. J. Org. Chem., 1996, 61(21), 7246-7247. (Pubitemid 126532308)
28. Nakamura, M.; Hirai, A.; Nakamura, E. Iron-catalyzed olefin carbometalation. J. Am. Chem. Soc., 2000, 122(5), 978-979.
29. Nakamura, M.; Matsuo, K.; Inoue, T.; Nakamura, E. Iron-catalyzed Regio- and Stereoselective ring opening of [2.2.1]- and [3.2.1]oxabicyclic alkenes with a Grignard reagent. Org. Lett., 2003, 5(8), 1373-1375. (Pubitemid 37162085)
30. Chambers, R.D.; Roche, A.J.; Rock, M.H. Polyhalogenated heterocyclic compounds. Part 41. Cycloaddition reactions involving hexafluorobut-2-yne and l,l,l,2,4,4,4-heptafluorobut-2-ene. J. Chem. Soc., Perkin Trans. 1, 1996, (11), 1095-1100.
31. Guidi, A.; Theurillat-Moritz, V.; Vogel, P.; Pinkerton, A.A. Enantiomerically pure Diels-Alder adducts of maleic anhydride to furfural acetals through thermodynamic control. Single crystal and molecular structure of (1S,4R,4′S,5′S)-1-4′,5′-dimethyldioxolan-2′-yl)- 5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene. Tetrahedron: Asymmetry, 1996, 7(11), 3153-3162. (Pubitemid 26394364)