Asian Journal of Organic Chemistry

Cover image for Vol. 3 Issue 9

Managing Editor: Richard Threlfall; Editorial Board Chairs: Sung Ho Kang, Keiji Maruoka, Deqing Zhang

Impact Factor: 2.292

ISI Journal Citation Reports © Ranking: 2013: 27/58 (Chemistry Organic)

Online ISSN: 2193-5815

Associated Title(s): Advanced Synthesis & Catalysis, Chemistry – An Asian Journal, European Journal of Organic Chemistry

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August 01, 2014

VIP: Synthesis of 19-Nor-Vitamin D A-Ring Synthons via Ring-Closing Olefin Metathesis

Yu Nagai, Tomoe Tanami, Junko Abe, Dr. Hazuki Nagai, Toru Hamamizu, Kaichiro Kominato, Keisuke Iida and Prof. Dr. Kazuo Nagasawa

Synthesis of 19-Nor-Vitamin D A-Ring Synthons via Ring-Closing Olefin MetathesisGive me a D: A synthetic method for making A-ring synthons for 19-nor-vitamin D was developed based on ring-closing olefin metathesis (RCM) with a linear precursor, followed by palladium-catalyzed isomerization of the endocyclic olefin product to give the target exocyclic olefin. PG=protecting group; TBS=tert-butyldimethylsilyl; Tf=trifluoromethanesulfonyl.

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Recently Published Articles

  1. Phosphotungstic Acid as an Efficient Catalyst for Allylation of Isatins and N-tert-Butyloxycarbonylamido Sulfones Under Solvent-Free Conditions

    Debashis Ghosh , S. Saravanan, Naveen Gupta, Sayed H. R. Abdi, Noor-ul H. Khan, Rukhsana I. Kureshy and Hari C. Bajaj

    Article first published online: 12 SEP 2014 | DOI: 10.1002/ajoc.201402130

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    Allyl in style: The present work discloses the highly efficient allylation of isatin derivatives as well as N-tert-butyloxycarbonylamido sulfones using phosphotungstic acid as the catalyst under ambient and solvent-free reaction conditions. The allylation products N-tert-butyloxycarbonyl (Boc) homoallyl amines were successfully epoxidized to get the corresponding epoxides in very good yields.

  2. Isolation and Characterization of 1 β-Acetoxypolygodial from Tasmannia lanceolata

    Ross M. Deans, Michael G. Gardiner, James Horne, Amos C. Hung, Christopher J. T. Hyland, Jeremy Just, Jason A. Smith and JieXiang Yin

    Article first published online: 9 SEP 2014 | DOI: 10.1002/ajoc.201402105

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    New from old: A natural product not previously reported has been isolated from Tasmannia lanceolata. This compound is related to the previously reported polygodial, but features an acetoxy group at the C1 position.

  3. Tandem Synthesis of Polysubstituted Pyridines via the Indium(III)-Triflate-Catalyzed Cycloaddition/Oxidative Aromatization of Blaise Reaction Intermediates with α,β-Unsaturated Ketones

    Zi Xuan, Dr. Kris Rathwell and Prof. Dr. Sang-gi Lee

    Article first published online: 9 SEP 2014 | DOI: 10.1002/ajoc.201402122

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    Three Sum to Six: A tandem, one-pot method for the synthesis of polysubstituted pyridines with complete control of the substitution pattern has been developed. Zinc bromide β-enamino esters from the Blaise reaction of nitriles with a Reformatsky reagent undergo Michael addition with conjugated ketones catalyzed by In(OTf)3. Final intramolecular cyclization and oxidative aromatization yields polysubstituted pyridines. Tf=trifluoromethanesulfonyl.

  4. Continuous Flow and Microwave-Assisted Vorbrüggen Glycosylations: Historical Perspective to High-Throughput Strategies

    Dr. Atul Manvar and Prof. Anamik Shah

    Article first published online: 4 SEP 2014 | DOI: 10.1002/ajoc.201402119

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    Historical to high-throughput: One of the most frequently used methods for glycosylation, the silyl Hilbert–Johnson reaction, or Vorbrüggen glycosylation, is summarized from the point of view of high-throughput microwave- and continuous-flow-assisted superheating. Especially, continuous-flow methods unlock an opportunity for developing synthetic processes through miniaturization.

  5. Copper-Free Sonogashira Coupling Reaction Catalyzed by PVC-Supported Triazine Palladium(II) Complex Under Aerobic Conditions

    Mohammad Bakherad, Ali Keivanloo, Amene Hadi and Maesoume Siavoshi

    Article first published online: 3 SEP 2014 | DOI: 10.1002/ajoc.201402125

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    Easy as PVC: A PVC-supported triazine palladium(II) complex is a highly active catalyst for the copper-free Sonogashira coupling of aryl halides with terminal alkynes at room temperature under aerobic conditions. This phosphine-free heterogeneous palladium catalyst can be easily recovered from the products and reused many times. DMF=N,N-dimethylformamide.