Studies on a Biomimetic Oxidative Dimerization Approach to the Hibarimicins

Overview

Journal Tetrahedron Lett

Publisher Elsevier

Specialty Chemistry

Date 2015 Aug 4

PMID 26236055

Citations 3

Authors

Ian M Romaine

Gary A Sulikowski

Affiliations

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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.

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References

Surry D, Spring D . The oxidation of organocuprates--an offbeat strategy for synthesis. Chem Soc Rev. 2006; 35(3):218-25. DOI: 10.1039/b508391p. View

Igarashi Y, Kajiura T, Furumai T, Hori H, Higashi K, Ishiyama T . Biosynthesis of hibarimicins. III. Structures of new hibarimicin-related metabolites produced by blocked mutants. J Antibiot (Tokyo). 2002; 55(1):61-70. DOI: 10.7164/antibiotics.55.61. View

Romaine I, Hempel J, Shanmugam G, Hori H, Igarashi Y, Polavarapu P . Assignment and stereocontrol of hibarimicin atropoisomers. Org Lett. 2011; 13(17):4538-41. PMC: 3163008. DOI: 10.1021/ol2017005. View

Liau B, Milgram B, Shair M . Total syntheses of HMP-Y1, hibarimicinone, and HMP-P1. J Am Chem Soc. 2012; 134(40):16765-72. PMC: 3468709. DOI: 10.1021/ja307207q. View

Sperry J, Sejberg J, Stiemke F, Brimble M . Biomimetic studies towards the cardinalins: synthesis of (+)-ventiloquinone L and an unusual dimerisation. Org Biomol Chem. 2009; 7(12):2599-603. DOI: 10.1039/b905077a. View

Kajiura T, FURUMAI T, Igarashi Y, Hori H, Higashi K, Ishiyama T . Signal transduction inhibitors, hibarimicins, A, B, C, D and G produced by Microbispora. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties. J Antibiot (Tokyo). 1998; 51(4):394-401. DOI: 10.7164/antibiotics.51.394. View

Bode S, Drochner D, Muller M . Synthesis, biosynthesis, and absolute configuration of vioxanthin. Angew Chem Int Ed Engl. 2007; 46(31):5916-20. DOI: 10.1002/anie.200701014. View

Drochner D, Huttel W, Nieger M, Muller M . Unselective phenolic coupling of methyl 2-hydroxy-4-methoxy-6-methylbenzoate--a valuable tool for the total synthesis of natural product families. Angew Chem Int Ed Engl. 2003; 42(8):931-3. DOI: 10.1002/anie.200390247. View

Huang C, Gevorgyan V . Synthesis of unsymmetrical o-biphenols and o-binaphthols via silicon-tethered Pd-catalyzed C-H arylation. Org Lett. 2010; 12(10):2442-5. PMC: 2873232. DOI: 10.1021/ol100924n. View

10.

Kajiura T, Furumai T, Igarashi Y, Hori H, Higashi K, Ishiyama T . Biosynthesis of hibarimicins. II. Elucidation of biosynthetic pathway by cosynthesis using blocked mutants. J Antibiot (Tokyo). 2002; 55(1):53-60. DOI: 10.7164/antibiotics.55.53. View

11.

Hori H, Kajiura T, Igarashi Y, Furumai T, Higashi K, Ishiyama T . Biosynthesis of hibarimicins. I. 13C-labeling experiments. J Antibiot (Tokyo). 2002; 55(1):46-52. DOI: 10.7164/antibiotics.55.46. View

12.

Surry D, Fox D, Macdonald S, Spring D . Aryl-aryl coupling via directed lithiation and oxidation. Chem Commun (Camb). 2005; (20):2589-90. DOI: 10.1039/b501939g. View

13.

Ashenhurst J . Intermolecular oxidative cross-coupling of arenes. Chem Soc Rev. 2010; 39(2):540-8. DOI: 10.1039/b907809f. View