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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.

SUBMITTER: Nicolaou KC 

PROVIDER: S-EPMC4530996 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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

Nicolaou K C KC   Shah Akshay A AA   Korman Henry H   Khan Tabrez T   Shi Lei L   Worawalai Wisuttaya W   Theodorakis Emmanuel A EA  

Angewandte Chemie (International ed. in English) 20150619 32

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. ...[more]

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