Chinese Journal of Chemistry

Cover image for Vol. 31 Issue 1

Special Issue: Dedicated to the Memory of Professor Wei-Shan Zhou

January, 2013

Volume 31, Issue 1

Pages 1–158

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Notes
    1. You have free access to this content
      Cover Picture: A Concise Total Synthesis of Amphidinin B (Chin. J. Chem. 1/2013) (page 1)

      Dongdong Wu, Jinlong Wu and Wei-min Dai

      Article first published online: 18 JAN 2013 | DOI: 10.1002/cjoc.201390000

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      The cover picture shows a concise total synthesis of amphidinin B, a polyketide metabolite isolated from the extracts of cultured marine dinoflagellates Amphidinium sp. (Y-56 strain). By playing a ring-forming trick, selective oxidative cleavage at the two monosubstituted alkene sites was achieved in the presence of the 1,1-disubstituted counterpart. Thus, starting from the triene precursor a ring-closing metathesis (RCM) reaction was performed to form the (12E)- and (12Z)-cycloalkenes. The latter were then subjected to regio- and stereoselective asymmetric dihydroxylation (AD), respectively, to produce the 12,13-diols. Further oxidative cleavage of the diols furnished amphidinin B. More details are discussed in the article by Dai et al. on page 105–110.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Notes
    1. You have free access to this content
      Working for Better! (pages 3–4)

      Guozhen Ji and Shengming Ma

      Article first published online: 18 JAN 2013 | DOI: 10.1002/cjoc.201390001

    2. You have free access to this content
      The Special Issue Dedicated to the Memory of Professor Wei-Shan Zhou (page 5)

      Guo-Qiang Lin and Ran Hong

      Article first published online: 18 JAN 2013 | DOI: 10.1002/cjoc.201390002

  3. Contents

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Notes
    1. Contents: Chin. J. Chem. 1/2013 (pages 6–13)

      Article first published online: 18 JAN 2013 | DOI: 10.1002/cjoc.201390003

  4. Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Notes
    1. Stereospecific Synthesis of Drospirenone (pages 15–17)

      Gang Deng, Zuogang Huang, Xiaolong Zhao, Zheng Li, Yuanchao Li and Biao Jiang

      Article first published online: 8 JAN 2013 | DOI: 10.1002/cjoc.201201147

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    2. A Formal Synthesis of Iridoid 9-Deoxygelsemide (pages 18–22)

      Yang Liu and Gang Zhao

      Article first published online: 8 JAN 2013 | DOI: 10.1002/cjoc.201201039

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      Starting from the known (S)-carvone, we have achieved the synthesis of the advanced intermediate 6 in 17 steps with an overall yield of 3.9%, which led to a formal total synthesis of 9-deoxygelsemide.

    3. Expedient Synthesis of (R)-Curcuphenol: A Chiral Pool Strategy (pages 23–26)

      Jing Feng, Guili Zhu, Bo Liu and Xiangdong Zhou

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201201024

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      Curcuphenol is an interesting terpenoid with diverse bioactivities. We report an expedient asymmetric synthesis of curcuphenol from citronellal which features only two purification operations in the overall six-step synthesis.

    4. Cu2O-Mediated Room Temperature Cyanation of Aryl Boronic Acids/Esters and TMSCN (pages 27–30)

      Yong Ye, Yanhua Wang, Pengtang Liu and Fushe Han

      Article first published online: 11 DEC 2012 | DOI: 10.1002/cjoc.201200711

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      A method for the efficient and reliable synthesis of aryl nitriles via the Cu2O-catalyed cross-coupling of aryl boronic acids or esters and TMSCN is presented. The room temperature operation paired with the use of cheap, readily available, and halogen-free Cu2O as catalysts makes the protocol an appealing option for aryl cyanations.

    5. An Efficient Semi-Synthetic Method to Construct Docetaxel via Sterically Crowded Linear Side Chain Esterification (pages 31–36)

      Xin Shen, Jidong Yang, Huaxing Zhan, Hu Wang, Shaohong Wu and Zili Chen

      Article first published online: 8 JAN 2013 | DOI: 10.1002/cjoc.201201142

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      An efficient semi-synthetic method was developed to construct docetaxel 1 by using N,N-di-Boc protected linear isoserine derivative 5 as the side chain source.

    6. Decarboxylative Alkylation of β-Keto Acids with Isochromans under Oxidative Conditions (pages 37–39)

      Yan Chen and Shi-Kai Tian

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201200994

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      A range of β-keto acids smoothly undergo decarboxylative alkylation with isochromans in the presence of 2,2,6,6-tetramethylpiperdine-1-oxoammonium hexafluorophosphate to give structurally diverse 1-acylmethylisochromans in moderate to excellent yields.

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Notes
    1. Stereoselective Total Synthesis of Tubulysin V (pages 40–48)

      Rui Wang, Ping Tian and Guoqiang Lin

      Article first published online: 11 DEC 2012 | DOI: 10.1002/cjoc.201200984

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      The total synthesis of tubulysin V was accomplished in 1.0% overall yield with linear 13 steps. Our synthetic strategy featured the following two reactions. One is zinc-mediated aza-Barbier reaction of (R)-N-tert-butanesulfinyl imine 8 with β-ester group functionalized allylic bromide 9 to afford the chiral homo-allylic amine 7; the other is to employ the methodology of aqueous indium-mediated aza-Barbier reaction previously developed by our group, giving the chiral homo-allylic amine 13 with high efficiency.

    2. One-pot Synthesis of Aromatic Fused 2,3-Dihydroindanone by Tandem Pauson-Khand/Michael/Henry Reaction (pages 49–54)

      Mingming Li, Ping Xing, Zuogang Huang and Biao Jiang

      Article first published online: 8 JAN 2013 | DOI: 10.1002/cjoc.201201118

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    3. Towards Stereochemical Control: Two Approaches for the Highly anti-Diastereoselective Construction of the Spirolactone Moieties of Some Stemona Alkaloids (pages 55–62)

      Shichuan Tuo, Xuekui Liu and Peiqiang Huang

      Article first published online: 11 DEC 2012 | DOI: 10.1002/cjoc.201200904

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      Completely anti-diastereoselective: This can be achieved by using bromine atom as a traceless directing group in the SmI2-mediated reductive coupling of α,β-unsaturated ester with ketones; or by the one-pot reaction of the organozinc reagent generated from bromomethacrylate with ketone. On the basis of these results, two approaches to the spirolactone moiety with anti-configuration (C-9/C-9a) found in some Stemona alkaloids were disclosed.

    4. A Scalable Synthesis of 6,19-Dihydroxyandrostenedione (pages 63–66)

      Yubo Yan, Ting Li, Tao Liu, Qingyu Dou, Kai Ding and Weisheng Tian

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201201023

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      A key intermediate, 6,19-dihydroxyandrostenedione, was successfully prepared in six steps from commercially available raw material. The process can be carried out on a large scale without laborious chromatography.

    5. Enantioselective Ring Opening of meso-Epoxides with Aromatic Amines Catalyzed by Dinuclear Magnesium Complexes (pages 67–71)

      Hongli Bao, Zheng Wang, Tianpa You and Kuiling Ding

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201201008

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      Dinuclear Mg complexes generated in situ from the combination of phenol-bridged bis(α,α-diarylprolinol) ligands and n-Bu2Mg were found to be efficient for the catalytic asymmetric ring opening of meso-epoxides with aniline derivatives as nucleophiles, affording the corresponding chiral β-amino alcohols in good yields with up to 90% ee.

    6. Dysoxylumasins A–F: Six New Limonoids from Dysoxylum mollissimum Bl. (pages 72–78)

      Jinbiao Xu, Gang Ni, Shengping Yang and Jianmin Yue

      Article first published online: 11 DEC 2012 | DOI: 10.1002/cjoc.201200838

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      Six new mexicanolide-type limonoids, dysoxylumasins A–F (16) together with eight known compounds, were isolated from the leaves and twigs of Dysoxylum mollissimum Bl. Their structures were established by the analyses of spectroscopic data.

    7. Four New Indole Alkaloids from Neolamarckia cadamba (pages 79–83)

      Lingli Liu, Shifei Li, Qiang Zhang, Feng Zhu, Wei Yang, Hongping He and Xiaojiang Hao

      Article first published online: 8 JAN 2013 | DOI: 10.1002/cjoc.201201016

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    8. Synthesis toward the Lindenane-type Sesquiterpenoid Monomer of Chlorahololide A (pages 84–92)

      Haizhen Zhang and Fajun Nan

      Article first published online: 11 DEC 2012 | DOI: 10.1002/cjoc.201200695

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      Starting from alcohol (2), and on the basis of Yamamoto rearrangement, intramolecular cyclopropanation reaction, 1,3-dipolar cyclization, and intramolecular Heck reaction, the Lindenane-type sesquiterpenoid fragement (20) of Chlorahololide A (1) has been synthesized in a linear sequence of 21 steps and an overall yield of 1.8%. The flexible synthetic route could generate further natural products of the Chloranthaceae family.

    9. Synthesis Study toward Mayamycin (pages 93–99)

      Kui Wu, Meining Wang, Qizheng Yao and Ao Zhang

      Article first published online: 8 JAN 2013 | DOI: 10.1002/cjoc.201201084

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      Natural product mayamycin is the first example in the angucycline class featuring a C-glycoside linkage at the C5-position of the benz[a]anthracenone core with remarkable biological activities. We successfully synthesized the two retrosynthetic fragments, but the final C-glycosylation did not occur. Instead, a two-ring less analog was success fully prepared, suggesting the steric effect played an important role in the synthesis of mayamycin.

    10. Antibiotic Metabolites from the Coral-Associated Actinomycete Streptomyces sp. OUCMDZ-1703 (pages 100–104)

      Peng Fu, Fandong Kong, Yuanfei Wang, Yi Wang, Peipei Liu, Guoying Zuo and Weiming Zhu

      Article first published online: 8 JAN 2013 | DOI: 10.1002/cjoc.201201062

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    11. A Concise Total Synthesis of Amphidinin B (pages 105–110)

      Dongdong Wu, Jinlong Wu and Wei-min Dai

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201201069

      Thumbnail image of graphical abstract

      The ester-linked triene I, designed for synthesis of 19-membered amphidinolide T1 and T3–T5 via the cycloalkene (12E)-II, has now been transformed into amphidinin B from both (12E)- and (12Z)-II through oxidative cleavage and subsequent oxidation.

    12. Biomimetic Cationic Cyclization toward ent-Kaurene-type Diterpenoids (pages 111–118)

      Lili Zhu and Ran Hong

      Article first published online: 8 JAN 2013 | DOI: 10.1002/cjoc.201201029

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      A chiral acetal-enabled and SnCl4-promoted biomimetic polyene cationic cyclization was followed by oxidation and a cascade process of Birch reduction and alkylation to complete a core skeleton of representative ent-kaurene diterpenoids.

    13. Design and Synthesis of Polymeric Chiral Bicyclo[3.3.0] Diene as Reusable Ligand for Rhodium-Catalyzed Asymmetric 1,4-Addition (pages 119–122)

      Hongyu Yang and Minghua Xu

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201201079

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      A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. By using polymeric diene, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones.

    14. First Total Synthesis of the Proposed Structures of Orisuaveolines A and B (pages 123–126)

      Jie Zhang, Shijun Da, Xiaolin Feng, Xiaoyi Chen, Jianhui Jiang and Ying Li

      Article first published online: 8 JAN 2013 | DOI: 10.1002/cjoc.201200986

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      First total synthesis of the proposed structures of β-indoloquinazoline alkaloids orisuaveolines A and B is reported. The key steps of the synthesis included a Pictet-Spengler reaction to build a six-member lactam which further transformed into target molecular by a one-pot condensation. The structures of our synthesized products were confirmed by 2D-NMR experiments.

    15. Microbial Transformation of Pregnane-3β,16β,20-triol by Cunninghamella echinulata (pages 127–131)

      Chenru Yang, Huafang Fan, Yuan Yuan and Jinming Gao

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201201080

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      Biotransformation of tigogenin-derived pregnane-3β,16β,20-triol (1) by Cunninghamella echinulata produced four new highly oxidized C21-steroids, pregnane-3β,14α,16β,20-tetrol (2), pregnane-3-oxo-14α,16β,20-triol (3), pregnane-3-oxo-7β,16β,20-triol (4), and pregnane-3β,7β,16β,20-tetrol (5).

    16. A Pd(II)-Catalyzed Oxidative Cyclization for the Preparation of Aryl-Fused Six-Membered Nitrogen Heterocycles with 2-Acetoxy Functionality (pages 132–138)

      Xiaolei Wang, Zhengxing Wu, Xiaowen Zhu, Chenghao Ye, Feng Jiang and Wanbin Zhang

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201200963

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      A Pd(II)-catalyzed oxidative cyclization of olefinic tosylamides was developed for the preparation of aryl-fused and N-containing six-membered heterocycles. Under optimized conditions the reaction proceeded with high activity and selectivity, with yields of up to 83% being obtained. This procedure provides a facile and efficient route to the aforementioned heterocycles with 2-acetoxy functionality.

    17. A Clear-Cut Synthesis of Arteannuin O (pages 139–142)

      Huijun Chen, Hongdong Hao and Yikang Wu

      Article first published online: 11 DEC 2012 | DOI: 10.1002/cjoc.201200926

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      Conversion of dihydroqinghao acid into natural arteannuin O was achieved via sequential oxidative lactonization, epoxidation, perhydrolysis of the expoxy ring and dimethyl sulfide reduction of the peroxyl group.

    18. Reactivity of AllylSmBr/HMPA: Facile Synthesis of 3-Aryl-1,2,4-benzotriazines (pages 143–148)

      Ruifeng Yin, Liejin Zhou, Huili Liu, Hui Mao, Xin Lü and Xiaoxia Wang

      Article first published online: 28 DEC 2012 | DOI: 10.1002/cjoc.201200989

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      3-Aryl-1,2,4-benzotriazines were conveniently prepared in moderate to good yields from 1,l-bis(benzotriazol-1-yl) methylarenes with allylsamarium bromide/hexamethyl-phosphramide (allylSmBr/HMPA). Preliminary results indicate that HMPA has the potential to enhance the reducing ability as well as to prohibit the nucleophicility of allylSmBr, thus making allylSmBr/HMPA as a promising single-electron transfer (SET) reagent.

  6. Notes

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communications
    6. Full Papers
    7. Notes
    1. Stereoselective Synthesis of (−)-Chloramphenicol, (+)-Thiamphenicol and (+)-Sphinganine via Chiral Tricyclic Iminolactone (pages 149–153)

      Qiong Li, Hongbo Zhang, Chenguang Li and Pengfei Xu

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201201093

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      Concise and efficient syntheses of (−)-chloramphenicol, (+)-thiamphenicol and (+)-sphinganine have been accomplished in practical four or three steps. The synthetic route featured in an aldol reaction between iminolactone 1a and 1b with aldehyde, which introduced the two continuous chiral centers within three target molecules.

    2. Synthesis and Cytotoxic Evaluation of Novel Platinum(II) Complexes with C2-Asymmetric and C2-Symmetric Chiral Vicinal Diamines (pages 154–158)

      Chen Zhang, Hongrui Liu, Qing Yang, Jun Chang and Xun Sun

      Article first published online: 8 JAN 2013 | DOI: 10.1002/cjoc.201201168

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      A series of new platinum(II) complexes with C2-asymmetric and C2-symmetric 1,2-diamines were designed and synthesized by convenient methods, involving samarium diiodide induced reductive coupling as the key step. The cytotoxicity of these analogs against four leukemia and three solid cancer cell lines was evaluated and the preliminary structure-activity relationship is also discussed. Flow cytometry data indicated that (R,R)-11a could obviously arrest leukemia K562 cells in G2/M phases.

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