Assignment and stereocontrol of hibarimicin atropoisomers.
AUTHORS
Romaine
IMIan M ,
Hempel
JE Jonathan E ,
Shanmugam
G Ganesh ,
Hori
H Hiroshi ,
Igarashi
Y Yasuhiro ,
Polavarapu
PL Prasad L ,
Sulikowski
GA Gary A .
Organic letters. 2011 9 2; 13(17).
4538-41
- PMID: 21812391[PubMed].
- PMCID: PMC3163008.
- NIHMSID: NIHMS315981
ABSTRACT
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.