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Assignment and Stereocontrol of Hibarimicin Atropoisomers

  作者 ROMAINE IAN M; HEMPEL JONATHAN E; SHANMUGAM GANESH; HORI HIROSHI; IGARASHI YASUHIRO; POLAVARAPU PRASAD L; SULIKOWSKI GARY A  
  选自 期刊  Organic Letters;  卷期  2011年13-17;  页码  4538-4541  
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[摘要]A stereochemical feature of the hibarimicins is a central biaryl (HMP-Y6) or aryl-quinone (hibarimicinone) incorporated as a single atropodiastereomer. Herein, a chiral resolution and deracemization process to access optically enriched biaryls aR-3 and aS-3 is described. From these atropoenantiomers the BCD-EFG ring system of HMP-Y6 is constructed [(+)-aR-7]. Comparison of CD spectra of aR-7 to HMP-Y6 leads to the assignment of HMP-Y6 and hibarimicin B atropoisomers as aR and aS, respectively.

 
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