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This process gave <20% yields of\n(4S,6S)-7 and (4R,6R)-7 because of the production\nof a cyclic carbamate side product, likely arising from intramolecular\ncyclization of the Boc group under Mitsunobu conditions. All other\nattempted reductions using AlH4 or BH4 reducing\nagents gave low diasteroselectivities or favored production of (4S,6R)-8 and (4R,6S)-8."},{"key":"ref8\/cit8","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/7.3.547"},{"key":"ref9\/cit9a","doi-asserted-by":"publisher","DOI":"10.1385\/0-89603-447-X:219"},{"key":"ref9\/cit9b","unstructured":"b A 40:1 CT DNA:ligand\nratio was utilized for these studies."},{"key":"ref10\/cit10","doi-asserted-by":"publisher","DOI":"10.4172\/2254-609X.100033"},{"key":"ref11\/cit11","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0176208"},{"key":"ref13\/cit13","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0037468"},{"key":"ref14\/cit14","doi-asserted-by":"publisher","DOI":"10.3390\/molecules21010054"},{"key":"ref15\/cit15","doi-asserted-by":"publisher","DOI":"10.1039\/C5NP00094G"},{"key":"ref16\/cit16a","first-page":"1052","volume":"12","author":"Sudlow G. D. J. B.","year":"1976","journal-title":"Mol. Pharmacol."},{"key":"ref16\/cit16b","unstructured":"bWe anticipate that\nthe conioidines bind in Sudlow site I because similar hydrophobic\norganics containing long n-alkyl chains such as octanoic,\nmyristic, lauric, and palmitic acids have all been shown to bind that\nsite:"},{"key":"ref16\/cit16c","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbapap.2017.04.004"},{"key":"ref16\/cit16d","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsb.2006.08.015"},{"key":"ref16\/cit16e","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.9b03407"},{"key":"ref16\/cit16f","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.6b00509"},{"key":"ref16\/cit16g","unstructured":"g The HSA\u2013conioidine\ntitration binding studies showed a strong quenching of the fluorescence\nof Trp 214, which is located in proximity to Sudlow site I. Furthermore,\nthe binding constant for (4R,6S)\nconioidine A (Kb = (1.6 \u00b1 0.3) \u00d7\n105 M\u20131) more closely resembles the binding\nconstant of the site I marker warfarin (Kb = 2.8 \u00d7 105 M\u20131) than that of\nthe site II marker ibuprofen (Kb = 2.9\n\u00d7 106 M\u20131)."},{"key":"ref17\/cit17","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21334"},{"key":"ref18\/cit18","doi-asserted-by":"publisher","DOI":"10.1093\/protein\/12.6.439"},{"key":"ref19\/cit19a","unstructured":"aWe\nsuggest that the binding of the conioidines to HSA occurs in a noncovalent\nfashion. To test the possibility of covalent reactivity by thiol conjugate\naddition to the enoate group of the conioidines, we exposed (4S,6S)-1 to ethanethiol (5\nmolar equiv) in CH2Cl2 for 48 h at 37 \u00b0C.\nNo reaction was observed. Furthermore, we exposed (4S,6S)-1 to ethanethiol (5 molar equiv)\nand a catalytic quantity (10 mol %) of the base DBU in CH2Cl2 for 48 h at 37 \u00b0C. Again, minimal conversion\ntook place. These observations indicate that the tigloate functional\ngroup of the conioidines is not highly reactive toward conjugate addition\nof thiols or their conjugate bases."},{"key":"ref19\/cit19b","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-009-0114-z"},{"key":"ref19\/cit19c","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsb.2007.12.004"},{"key":"ref19\/cit19d","doi-asserted-by":"publisher","DOI":"10.1021\/ja908878n"},{"key":"ref19\/cit19e","doi-asserted-by":"publisher","DOI":"10.1042\/BJ20090913"},{"key":"ref20\/cit20","doi-asserted-by":"publisher","DOI":"10.1021\/bm049668m"},{"key":"ref21\/cit21","doi-asserted-by":"publisher","DOI":"10.1016\/S0165-022X(00)00143-3"},{"key":"ref22\/cit22","doi-asserted-by":"publisher","DOI":"10.1016\/j.jchromb.2011.05.020"},{"key":"ref23\/cit23a","doi-asserted-by":"publisher","DOI":"10.1016\/0022-1759(83)90303-4"},{"key":"ref23\/cit23b","doi-asserted-by":"publisher","DOI":"10.3727\/095535491820873191"},{"key":"ref23\/cit23c","unstructured":"cSee Supporting Information for preliminary MTT assay\nresults for the dosing of MCF-7 cells with (4R,6R)-1 and (4S,6S)-1."},{"key":"ref24\/cit24","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b02393"},{"key":"ref25\/cit25","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201402232"}],"container-title":["Journal of Natural Products"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jnatprod.0c00871","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,24]],"date-time":"2023-04-24T02:02:00Z","timestamp":1682301720000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.jnatprod.0c00871"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,10,9]]},"references-count":39,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2020,10,23]]}},"alternative-id":["10.1021\/acs.jnatprod.0c00871"],"URL":"https:\/\/doi.org\/10.1021\/acs.jnatprod.0c00871","relation":{},"ISSN":["0163-3864","1520-6025"],"issn-type":[{"type":"print","value":"0163-3864"},{"type":"electronic","value":"1520-6025"}],"subject":[],"published":{"date-parts":[[2020,10,9]]}}}