Literature DB >> 26236055

Studies on a biomimetic oxidative dimerization approach to the hibarimicins.

Ian M Romaine1, Gary A Sulikowski1.   

Abstract

Nature utilizes dimerization as a method of producing structurally complex metabolites. The microbial metabolites known collectively as the hibarimicins are one example of complex natural products produced biosynthetically by dimerization of a phenolic aromatic polyketide. Described in this communication are model studies aimed at demonstrating regiocontrolled oxidative dimerization of phenolic ring systems related to the biosynthetic precursor of the hibarimicin family of natural products.

Entities:  

Keywords:  Oxidation; Oxidative dimerization; Quinone; Regioselectivity; Silicon tether

Year:  2015        PMID： 26236055      PMCID： PMC4518470          DOI： 10.1016/j.tetlet.2015.01.127

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  13 in total

1.  Unselective phenolic coupling of methyl 2-hydroxy-4-methoxy-6-methylbenzoate--a valuable tool for the total synthesis of natural product families.

Authors:  Daniel Drochner; Wolfgang Hüttel; Martin Nieger; Michael Müller
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-24       Impact factor: 15.336

2.  Synthesis of unsymmetrical o-biphenols and o-binaphthols via silicon-tethered Pd-catalyzed C-H arylation.

Authors:  Chunhui Huang; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

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

Authors:  David S Surry; David R Spring
Journal:  Chem Soc Rev       Date:  2005-12-16       Impact factor: 54.564

4.  Synthesis, biosynthesis, and absolute configuration of vioxanthin.

Authors:  Silke E Bode; Daniel Drochner; Michael Müller
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Assignment and stereocontrol of hibarimicin atropoisomers.

Authors:  Ian M Romaine; Jonathan E Hempel; Ganesh Shanmugam; Hiroshi Hori; Yasuhiro Igarashi; Prasad L Polavarapu; Gary A Sulikowski
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

6.  Total syntheses of HMP-Y1, hibarimicinone, and HMP-P1.

Authors:  Brian B Liau; Benjamin C Milgram; Matthew D Shair
Journal:  J Am Chem Soc       Date:  2012-09-26       Impact factor: 15.419

7.  Biosynthesis of hibarimicins. II. Elucidation of biosynthetic pathway by cosynthesis using blocked mutants.

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

8.  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

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
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  3 in total

1.  Total Synthesis of Aurofusarin: Studies on the Atropisomeric Stability of Bis-Naphthoquinones.

Authors:  Chao Qi; Wenyu Wang; Kyle D Reichl; James McNeely; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-29       Impact factor: 15.336

Review 2.  Laccase-mediated synthesis of bioactive natural products and their analogues.

Authors:  Nunzio Cardullo; Vera Muccilli; Corrado Tringali
Journal:  RSC Chem Biol       Date:  2022-04-18

3.  Co-culture of the fungus Fusarium tricinctum with Streptomyces lividans induces production of cryptic naphthoquinone dimers.

Authors:  Mariam Moussa; Weaam Ebrahim; Michele Bonus; Holger Gohlke; Attila Mándi; Tibor Kurtán; Rudolf Hartmann; Rainer Kalscheuer; Wenhan Lin; Zhen Liu; Peter Proksch
Journal:  RSC Adv       Date:  2019-01-11       Impact factor: 4.036
  3 in total

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