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acetate added alcohol 43 alcohols 9 alkylation allylic alcohol allylic alcohol l5 allylic cation alumina angular methyl group anhydrous anhydrous formic acid anhydrous magnesium sulfate anhydrous sodium sulfate authentic axial bicarbonate brine Carbowax column cation cation 66 cationic center colorless oil combined ether extracts conformation cyclization cyclization conditions cyclization of alcohol cyclization products dienol double bond dried over anhydrous elution epimer epimeric ethanol evaporatively distilled extracted with ether extracts were washed Figure formic acid give hydrocarbon hydrogenation infrared spectrum isolated isomer isomeric Jones reagent ketone ketone 57 lithium aluminum hydride magnesium sulfate mmoles nmr spectrum olefin oxidation peak area pentane prepared protons reaction mixture Recrystallization reflux Removal of solvent room temperature rotory evaporation sample sodium sulfate solution solvent was removed stereochemistry stereoselective tetracyclic alcohol tetrahydrofuran thin layer chromatography thioketal three protons trans tricyclic vapor phase chromatography vinyl protons washed water water and extracted yield