Chinese Journal of Chemistry

Cover image for Vol. 33 Issue 6

Special Issue: Resource Chemistry

June, 2015

Volume 33, Issue 6

Pages 617–687

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Retraction
    1. You have free access to this content
      Cover Picture: BF3·Et2O Promoted Sulfuration of Steroidal Sapogenins (Chin. J. Chem. 6/2015) (page 617)

      Jun Wang, Jingjing Wu and Weisheng Tian

      Article first published online: 17 JUN 2015 | DOI: 10.1002/cjoc.201590013

      Thumbnail image of graphical abstract

      The cover picture shows a direct synthesis of 26-thio steroidal sapogenins from natural steroidal sapogenins, which serve as an important kind of resource compounds and basic starting materials in steroidal pharmaceutical industry. This method was based on a key and magic BF3·Et2O promoted C-26 sulfuration of steroidal sapogenins, which resulted in the direct replacement of the oxygen atom in F-ring of steroidal sapogenins by sulfur. The synthesis not only provides a concise method for 26-thio steroidal sapogenins, but also presents an ideal model of the utilization of steroidal sapogenins. More details are discussed in the article by Wang and Tian et al. on page 632–636.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Retraction
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      Resource Chemistry (pages 619–620)

      Weisheng Tian and Yong Shi

      Article first published online: 17 JUN 2015 | DOI: 10.1002/cjoc.201590014

  3. Contents

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Retraction
    1. Contents: Chin. J. Chem. 6/2015 (pages 621–624)

      Article first published online: 17 JUN 2015 | DOI: 10.1002/cjoc.201590015

  4. Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Retraction
    1. Synthesis of Tribolure, the Common Aggregation Pheromone of Four Tribolium Flour Beetles (pages 627–631)

      Chao Wang, Chengyu He, Yong Shi, Hua Xiang and Weisheng Tian

      Article first published online: 10 JUN 2015 | DOI: 10.1002/cjoc.201500334

      Thumbnail image of graphical abstract

      A synthesis of tribolure, which divided the four stereoisomers of tribolure into two sets of epimers and created the two required C4 stereocenters from the same chiron, is described. Our strategy may facilitate the development of synthetic design and find more applications in pheromone synthesis.

    2. BF3·Et2O Promoted Sulfuration of Steroidal Sapogenins (pages 632–636)

      Jun Wang, Jingjing Wu and Weisheng Tian

      Article first published online: 2 JUN 2015 | DOI: 10.1002/cjoc.201500300

      Thumbnail image of graphical abstract

      The reaction between steroidal sapogenins and hydrogen sulfide catalyzed by BF3·Et2O is described. The thiodiosgenin and thiotigogenin comprising a sulfur atom on the F ring have been synthesized under this mild reaction conditions.

    3. A Formal Synthesis of Betamethasone (pages 637–642)

      Shasha Wang, Yong Shi and Weisheng Tian

      Article first published online: 2 JUN 2015 | DOI: 10.1002/cjoc.201500335

      Thumbnail image of graphical abstract

      A formal synthesis of betamethasone from pregnane-3β,16β,20S-triol is described. Key transformations are a bromination-acetylation of triol, an SN2 reaction of the resulting C16α-bromide with dimethylcopperlithium to get the required C16β-methyl group, and a double hydroxylation to prepare the dihydroxyacetone side chain.

    4. Methyl Group in Isocopalane Derivative Showed an Unusual Negative 1H NMR Chemical Shift (pages 643–645)

      Xiong Xiao, Tianqi Chen, Fengfeng Zhang, Jiagao Cheng, Peiying Wu, Jiangmeng Ren and Bubing Zeng

      Article first published online: 5 MAY 2015 | DOI: 10.1002/cjoc.201500187

      Thumbnail image of graphical abstract

      An unusual negative 1H NMR chemical shift of methyl group in condensation product of isocopalane diterpenoid with p-toluenesulfonyl hydrazide was discovered. 2D NMR, computational studies and single-crystal X-ray diffraction analysis were used to determine the real conformation.

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Retraction
    1. Towards Reaction Control: An Expeditious Access to Racemic 5-Substituted Tetramates and 5-Substituted Tetramic Acids from Malimides (pages 655–662)

      Pei-Qiang Huang, Wei Ou and Jian-Liang Ye

      Article first published online: 12 DEC 2014 | DOI: 10.1002/cjoc.201400762

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      A versatile and divergent two-step transformation of malimides to racemic tetramates and tetramic acids is described. The method consists of Grignard reagent addition with malimides, and concentrated HCl-promoted chemoselective transformations of the latter.

    2. Synthesis of C1–C9 Domain of the Nominal Didemnaketal A (pages 663–668)

      Shunji Zhang, Yong Shi and Weisheng Tian

      Article first published online: 12 JUN 2015 | DOI: 10.1002/cjoc.201500256

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      Herein we describe a synthesis of C1–C9 domain 2 of the proposed structure of didemnaketal A, a natural product with important bioactivities, from potassium (2R,4R)-2,5-dihydroxy-4-methylpentanoate 5. Sharpless asymmetric dihydroxylation introduced the chiral vicinal diol and chelation-controlled allylation established another chiral OH.

    3. Semisynthesis of Azedarachol from Pregnanetriol, a Degradative Product of Tigogenin (pages 669–673)

      Dongshan Zhang, Yong Shi and Weisheng Tian

      Article first published online: 10 JUN 2015 | DOI: 10.1002/cjoc.201500231

      Thumbnail image of graphical abstract

      Described herein is a semisynthesis of azedarachol from pregnanetriol, which featured a symbiotic elimination/deprotection process, an oxidation/reduction procedure for reversing C20 configuration, and a dehydration-dihydroxylation process to introduce 2,3-cis-diol. This synthesis also discloses some interesting selectivities of 16,20-diol unit.

    4. Syntheses of (R)- and (S)-3-Methylheptanoic Acids (pages 674–678)

      Shunji Zhang, Yong Shi and Weisheng Tian

      Article first published online: 5 MAY 2015 | DOI: 10.1002/cjoc.201400861

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      Both enantiomers of 3-methylheptanoic acid have been synthesized from chiral methyl molecules which were derived from (R)-4-methyl-δ-valerolactone (5). A wide variety of chiral 3-methyl alkanoic acids can also be synthesized by the methods described herein.

    5. An Efficient Synthesis of (+)-Subersic Acid (pages 679–682)

      Jing Wang, Peiqiang Wang, Jue Li, Peiying Wu, Jiangmeng Ren and Bubing Zeng

      Article first published online: 10 JUN 2015 | DOI: 10.1002/cjoc.201500219

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      A seven-step synthetic route was developed to synthesize (+)-subersic acid from (−)-Sclareol. The cross coupling of the diterpene with the arene fragment using the arylation of allylic acetate followed by β-acetoxy elimination type Heck reaction was acted as the key reaction.

    6. Synthesis of (R)-(−)-Muscone from (R)-5-Bromo-4-methylpentanoate: A Chiron Approach (pages 683–687)

      Junwei Shen, Yong Shi and Weisheng Tian

      Article first published online: 9 MAR 2015 | DOI: 10.1002/cjoc.201400862

      Thumbnail image of graphical abstract

      Using methyl (R)-5-bromo-4-methylpentanoate, we have accomplished a synthesis of (R)-muscone, a natural macrocyclic musk, based on chiral pool strategy.

  6. Retraction

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Retraction
    1. You have free access to this content
      Retraction: A Facile Synthetic Route to New Fluorinated Building-Blocks of 1-Fluoroalkynes and 1-Fluorodiynes

      Cuibo Liu, Hai Ma, Jing Nie and Junan Ma

      Article first published online: 17 JUN 2015 | DOI: 10.1002/cjoc.201511445

      This article corrects:

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