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EXPLORATION OF THE CHEMISTRY OF ALKYNES AND SELECTFLUOR. SEARCH FOR CYTOTOXIC AGENTS FROM THE AMAZONIAN RAINFOREST Zhuang Jin March 5, 2012 Vicinal dithioethers and alkenyl thioethers were synthesized under environmentally friendly conditions using alkyne and thiol in water. Alkynes were also used to develop a multibond-fonning reaction that fonned cyclic ketones or ketoesters through a goldcatalyzed intramolecular oxygen transfer isomerization of 2-alkynyl-l ,5-diketones or 2alkyny 1-5 -ketoesters. The investigation of Selectfluor chemistry yielded a highly stereoselective synthesis of fluoroalky (E)-a,B-unsaturated ketones from allenyl esters, through a gold-catalyzed rearrangement that produced an intennediate dienyl ester. When Selectfluor was combined with copper, it produced two oxidative systems, F-TEDA-BF4 and F-TEDAPF 6, both of which efficiently converted amides into imides at room temperature in short time, but whereas the fonner employed stoichiometric amounts of copper(I), the latter only needed catalytic amounts. The bioassay-directed fractionation of Physalis angulata L. afforded three new antiproliferative withanolides: physangulidines A, B and C. Each has shown significant

Exploration of the chemistry of alkynes and Selectfluor : search for cytotoxic agents from the Amazonian rainforest.