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  • Title: Toward the development of a general chiral auxiliary. A total synthesis of (+)-tetronolide via a tandem ketene-trapping [4 + 2] cycloaddition strategy.
    Author: Boeckman RK, Shao P, Wrobleski ST, Boehmler DJ, Heintzelman GR, Barbosa AJ.
    Journal: J Am Chem Soc; 2006 Aug 16; 128(32):10572-88. PubMed ID: 16895426.
    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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