Jonathan Hempel
Last active: 3/25/2014

Assignment and stereocontrol of hibarimicin atropoisomers.

Romaine IM, Hempel JE, Shanmugam G, Hori H, Igarashi Y, Polavarapu PL, Sulikowski GA
Org Lett. 2011 13 (17): 4538-41

PMID: 21812391 · PMCID: PMC3163008 · 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.

MeSH Terms (4)

Glycosides Molecular Conformation Naphthacenes Stereoisomerism

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