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Literature DB >> 21812391

Assignment and stereocontrol of hibarimicin atropoisomers.

Ian M Romaine¹, Jonathan E Hempel, Ganesh Shanmugam, Hiroshi Hori, Yasuhiro Igarashi, Prasad L Polavarapu, Gary A Sulikowski.

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.

Entities: Chemical Disease Gene Species

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Year: 2011 PMID： 21812391 PMCID： PMC3163008 DOI： 10.1021/ol2017005

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

29 in total

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2. Atroposelective synthesis of axially chiral biaryl compounds.

Authors: Gerhard Bringmann; Anne J Price Mortimer; Paul A Keller; Mary J Gresser; James Garner; Matthias Breuning
Journal: Angew Chem Int Ed Engl Date: 2005-08-26 Impact factor: 15.336

3. The oxidation of organocuprates--an offbeat strategy for synthesis.

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4. Dynamic thermodynamic resolution: advantage by separation of equilibration and resolution.

Authors: Won Koo Lee; Yong Sun Park; Peter Beak
Journal: Acc Chem Res Date: 2009-02-17 Impact factor: 22.384

5. Signal transduction inhibitors, hibarimicins A, B, C, D and G produced by Microbispora. II. Structural studies.

Authors: H Hori; Y Igarashi; T Kajiura; T Furumai; K Higashi; T Ishiyama; M Uramota; Y Uehara; T Oki
Journal: J Antibiot (Tokyo) Date: 1998-04 Impact factor: 2.649

6. Biosynthesis of hibarimicins. III. Structures of new hibarimicin-related metabolites produced by blocked mutants.

Authors: Yasuhiro Igarashi; Takayuki Kajiura; Tamotsu Furumai; Hiroshi Hori; Kazuaki Higashi; Tadayuki Ishiyama; Masakazu Uramoto; Yoshimasa Uehara; Toshikazu Oki
Journal: J Antibiot (Tokyo) Date: 2002-01 Impact factor: 2.649

7. Studies into the stereoselectivity of tartrate-derived dienophiles.

Authors: Wei-Der Lee; Kwangho Kim; Gary A Sulikowski
Journal: Org Lett Date: 2005-04-28 Impact factor: 6.005

8. Optically active (aR)- and (aS)-linear and vaulted biaryl ligands: deracemization versus oxidative dimerization.

Authors: Gang Hu; Daniel Holmes; Brina Fay Gendhar; William D Wulff
Journal: J Am Chem Soc Date: 2009-10-14 Impact factor: 15.419

9. Biomimetic studies towards the cardinalins: synthesis of (+)-ventiloquinone L and an unusual dimerisation.

Authors: Jonathan Sperry; Jimmy J P Sejberg; Frank M Stiemke; Margaret A Brimble
Journal: Org Biomol Chem Date: 2009-04-28 Impact factor: 3.876

10. Signal transduction inhibitors, hibarimicins, A, B, C, D and G produced by Microbispora. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties.

Authors: T Kajiura; T Furumai; Y Igarashi; H Hori; K Higashi; T Ishiyama; M Uramoto; Y Uehara; T Oki
Journal: J Antibiot (Tokyo) Date: 1998-04 Impact factor: 2.649

4 in total