Toward the Development of a General Chiral Auxiliary. A Total Synthesis of (+)-Tetronolide via a Tandem Ketene-Trapping [4 + 2] Cycloaddition Strategy

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• 作者：Robert K. Boeckman ; Jr. ; Pengcheng Shao ; Stephen T. Wrobleski ; Debra J. Boehmler ; Geoffrey R. Heintzelman ; Antonio. J. Barbosa
• 刊名：Journal of the American Chemical Society
• 出版年：2006
• 出版时间：August 16, 2006
• 年：2006
• 卷：128
• 期：32
• 页码：10572 - 10588
• 全文大小：378K
• 年卷期：v.128,no.32(August 16, 2006)
• ISSN：1520-5126

文摘

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 camphorauxiliary-directed asymmetric alkylation and the enantioselective preparation of acyclic mixed acetals bearingchirality at the acetal center, and the highly efficient connection of the two major precursors via a ketene-trapping/intramolecular [4 + 2] cycloaddition strategy.