Total Synthesis and Structural Revision of Antibiotic CJ-16,264

Abstract

The total synthesis and structural revision of antibiotic CJ-16,264 is described. Starting with citronellal, the quest for the target molecule featured a novel bis-transannular Diels-Alder reaction that casted stereoselectively the decalin system and included the synthesis of six isomers before demystification of its true structure.

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Nicolaou, K.C., Shah, Akshay A., Korman, Henry, et al.. "Total Synthesis and Structural Revision of Antibiotic CJ-16,264." Angewandte Chemie, 54, no. 32 (2015) Wiley: 9203-9208. http://dx.doi.org/10.1002/anie.201504337.

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