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RESULTS AND DISCUSSION
SUMMARY AND PROJECTIONS
3 other sections not shown
13C NMR acid-base extraction added dropwise alcohol aldehyde aldehyde 83 aqueous phase benzene brevetoxins BTX-B carbon Chem CIMS colorless oil combined ether extracts combined ethyl acetate combined hexane concentrated in vacuo crude product cyclization diol DMSO dried and concentrated enantiomeric excess enol ether enyne epoxide epoxyol ester ethanol ethyl acetate ethyl acetate extracts extracted with ether extracted with hexane extracts were dried film fluoride geraniol geraniol oxide H NMR hexane hydroxide intermediate Jones reagent Kugelrohr lactone lOmL mixture was stirred NaCl and extracted NMR dg benzene nucleophiles oil was flash pentane phase was extracted phase was saturated product was flash reacted reaction mixture removed in vacuo Retrosynthetic Analysis ring saturated aqueous saturated with NaCl silyl sodium solution was stirred solvent starting material stirred at 78°C stirred at rt stirred solution Swern Swern oxidation synthetic Tetrahedron Lett tetronic acids tosylate triethylamine trifluoroacetic anhydride warmed to rt y-lactone