Asian Journal of Organic Chemistry

Cover image for Vol. 3 Issue 8

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. Use of a Desymmetrized meso Molecule as a Chiral Ligand: Development of Chiral N-Heterocyclic Carbene Ligands for Asymmetric Allylic Arylations with Grignard Reagents

    Shin Ando, Hirofumi Matsunaga and Tadao Ishizuka

    Article first published online: 13 AUG 2014 | DOI: 10.1002/ajoc.201402089

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    Broken symmetry: The desymmetrization of a meso molecule was used for the development of a chiral N-heterocyclic carbene (NHC) ligand. The stereocontrol in asymmetric allylic arylations was improved to 89 % ee via derivatization studies. The resultant copper catalyst was effective at the level of 0.05 mol % loading for gram-scale reactions.

  2. Decarboxylative C[BOND]P Coupling of o-Nitrobenzoic Acids with H-Phosphonates

    Junchen Li, Xiaojing Bi, Prof. Hongmei Wang and Prof. Junhua Xiao

    Article first published online: 12 AUG 2014 | DOI: 10.1002/ajoc.201402088

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    Go with the ortho: ortho-Nitrobenzoic acids with various functional groups undergo decarboxylative C[BOND]P coupling with H-phosphonates by using a bimetallic Pd/Ag catalytic system for the preparation of biologically and synthetically important aryl phosphonates. DMF=N,N-dimethylformamide.

  3. Copper(I)-Oxide-Mediated Cyanation of Arenediazonium Tetrafluoroborates with Trimethylsilyl Cyanide: A Method for Synthesizing Aromatic Nitriles

    Wen-Bin Xu, Qing-Hui Xu, Zhen-Fa Zhang and Ji-Zhen Li

    Article first published online: 11 AUG 2014 | DOI: 10.1002/ajoc.201402084

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    Goodnit-rile: A Cu2O-mediated cross coupling of arenediazonium tetrafluoroborates with trimethylsilyl cyanide (TMSCN) to form aromatic nitriles is presented. This method provides appealing and convenient access to aromatic nitriles compared with the traditional Sandmeyer reaction with toxic CuCN via nucleophilic substitution. A variety of functional groups are well tolerated in moderate to high yield in this protocol.

  4. Revisiting the Saito Photochemical Reduction and the Development of a One-Pot Deoxygenation of Alcohols

    Prof. Dr. Ryosuke Matsubara, Yong-Soon Shin, Toshiyuki Shimada and Prof. Dr. Masahiko Hayashi

    Article first published online: 11 AUG 2014 | DOI: 10.1002/ajoc.201402123

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    Concentrate on this one: The Saito photochemical reduction of m-(trifluoromethyl)benzoates has been revisited. In contrast to the conventional conditions, the developed method eliminates the formation of alkene byproducts at high concentrations. Combining direct esterification and the Saito photochemical reduction, a one-pot deoxygenation process of alcohols has also been developed. LED=light-emitting diode; TsOH=4-toluenesulfonic acid.

  5. Synthetic Studies Toward Harringtonolide

    Dr. Zhiqiang Ma, Dr. Bin Cheng and Prof. Dr. Hongbin Zhai

    Article first published online: 6 AUG 2014 | DOI: 10.1002/ajoc.201402116

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    It’s got potential: An efficient synthesis of the oxo-bridged 7/6-bicyclic precursor 4 that is potentially useful for the construction of harringtonolide (1) has been realized through a [4+3] cycloaddition reaction as the key transformation.

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