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Literature DB >> 29658717

Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Xiaowei Wu¹, Takayuki Iwata¹, Adam Scharf¹, Tian Qin¹, Kyle D Reichl¹, John A Porco¹.

Abstract

The first synthesis of the chromanone lactone dimer gonytolide A has been achieved employing vanadium(V)-mediated oxidative coupling of the monomer gonytolide C. An o-bromine blocking group strategy was employed to favor para- para coupling and to enable kinetic resolution of (±)-gonytolide C. Asymmetric conjugate reduction enabled practical kinetic resolution of a chiral, racemic precursor and the asymmetric synthesis of (+)-gonytolide A and its atropisomer.

Entities: Chemical Disease Gene Species

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Year: 2018 PMID： 29658717 PMCID： PMC5943148 DOI： 10.1021/jacs.8b02535

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

74 in total

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7. Enantioselective fluorination mediated by cinchona alkaloid derivatives/Selectfluor combinations: reaction scope and structural information for N-fluorocinchona alkaloids.

Authors: N Shibata; E Suzuki; T Asahi; M Shiro
Journal: J Am Chem Soc Date: 2001-07-25 Impact factor: 15.419

Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

1. Vanadium in Modern Organic Synthesis.

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5. Dynamic kinetic resolution of alpha,beta-unsaturated lactones through asymmetric copper-catalyzed conjugate reduction: application to the total synthesis of eupomatilone-3.

6. Catalytic Asymmetric Bromination of Unfunctionalized Olefins with H2O as a Nucleophile.

7. Enantioselective fluorination mediated by cinchona alkaloid derivatives/Selectfluor combinations: reaction scope and structural information for N-fluorocinchona alkaloids.

8. Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.

9. Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes.

10. Scalable total synthesis and biological evaluation of haouamine A and its atropisomer.

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Review 2. Synthetic Applications of Oxidative Aromatic Coupling-From Biphenols to Nanographenes.

3. Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones.