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^*

来源：Organic Letters, 2011, 13(17): 4538-4541.

DOI：10.1021/ol2017005

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.

• 出版日期2011-9-2