Toward the Development of a General Chiral Auxiliary. A Total Synthesis of (+)-Tetronolide via a Tandem Ketene-Trapping [4 + 2] Cycloaddition Strategy
Journal of the American Chemical Society2006Vol. 128(32), pp. 10572–10588
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Robert K. Boeckman, Pengcheng Shao, Stephen T. Wrobleski, Debra J. Boehmler, Geoffrey R. Heintzelman, Antonio. J. Barbosa
Abstract
A highly convergent, enantioselective total synthesis of the aglycone of the tetrocarcins, (+)-tetronolide, is described. The synthesis highlights the use of several new methods, including camphor auxiliary-directed asymmetric alkylation and the enantioselective preparation of acyclic mixed acetals bearing chirality at the acetal center, and the highly efficient connection of the two major precursors via a ketene-trapping/intramolecular [4 + 2] cycloaddition strategy.
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