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N-N-Coupled Indolo-sesquiterpene Atropo-Diastereomers from a Marine-Derived Actinomycete

  作者 ZHANG QINGBO; MANDI ATTILA; LI SUMEI; CHEN YUCHAN; ZHANG WENJUN; TIAN XINPENG; ZHANG HAIBO; LI HUIXIAN; ZHANG WEIMIN; ZHANG SI; JU JIANHUA; KURTAN TIBOR; ZHANG CHANGSHENG  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2012年-27;  页码  5256-5262  
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[摘要]Four new indolo-sesquiterpenes dixiamycins A (1) and B (2), oxiamycin (3), and chloroxiamycin (4) were isolated from a marine-derived Actinomycete and characterized, together with the known compound xiamycin A (5). Dixiamycins A (1) and B (2) are the first examples of atropisomerism of naturally occurring N-N-coupled atropo-diastereomers, with a dimeric indolo-sesquiterpene skeleton and a stereogenic N-N axis between sp3-hybridized nitrogen atoms. Solution TDDFT ECD calculations were utilized to ascertain the axial chirality of 1 and 2, and rotational barriers and transitions states of the inversion were calculated. Oxiamycin (3) contains a seven-membered 2,3,4,5-tetrahydrooxepine ring. The two dimeric compounds 1 and 2 showed better antibacterial activities than the monomers 35.

 
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