Enantioselective Total Synthesis of (S)-Bisoranjidiol, an Axially Chiral Bisanthraquinone

被引:42
|
作者
Podlesny, Erin E. [1 ]
Kozlowski, Marisa C. [1 ]
机构
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
BINAPHTHYL POLYMERS; STEREOCHEMISTRY; COMPLEXES; PIGMENTS; TANDEM;
D O I
10.1021/ol3001365
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first enantioselective total synthesis of the bisanthraquinone (S)-bisoranjidiol and an unnatural regioisomer has been accomplished. Key features of the synthesis include the asymmetric oxidative biaryl coupling of a hindered 8-substituted 2-naphthol, selective para-quinone formation, and regioselective tandem Diels-Alder/aromatization reactions.
引用
收藏
页码:1408 / 1411
页数:4
相关论文
共 50 条
  • [1] Divergent Approach to the Bisanthraquinone Natural Products: Total Synthesis of (S)-Bisoranjidiol and Derivatives from Binaphtho-para-quinones
    Podlesny, Erin E.
    Kozlowski, Marisa C.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02): : 466 - 476
  • [2] Asymmetric total synthesis of (S)-bisoranjidiol
    Podlesny, Erin E.
    Kozlowski, Marisa C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [3] Progress on the Enantioselective Synthesis of Axially Chiral Cycloalkylidenes
    Wang, Zi-Lu
    Xu, Yun-He
    SYNTHESIS-STUTTGART, 2024, 56 (08): : 1259 - 1272
  • [4] Catalytic enantioselective synthesis of axially chiral allenes
    Ogasawara, Masamichi
    TETRAHEDRON-ASYMMETRY, 2009, 20 (03) : 259 - 271
  • [6] Catalytic Enantioselective Synthesis of Axially Chiral Diarylmethylidene Indanones
    Kumar, Prashant
    Shirke, Rajendra P.
    Yadav, Sonu
    Ramasastry, S. S., V
    ORGANIC LETTERS, 2021, 23 (12) : 4909 - 4914
  • [7] Total synthesis of axially-chiral cannabinols
    Grenning, Alexander
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [8] Research Progress on the Catalytic Enantioselective Synthesis of Axially Chiral Allenes by Chiral Organocatalysts
    Li, Qing Han
    Jiang, Xin
    Wu, Kun
    Luo, Rui Qiang
    Liang, Meng
    Zhang, Zhi Hao
    Huang, Zhe Yao
    CURRENT ORGANIC CHEMISTRY, 2020, 24 (06) : 694 - 708
  • [9] Enantioselective Reaction of Diynes and Multiynes for the Synthesis of Axially Chiral Compounds
    Zhu, Xin-Qi
    Li, Yu-Chao
    Ye, Long-Wu
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (01)
  • [10] Copper-Catalyzed Enantioselective Synthesis of Axially Chiral Allenes
    Li, Hailing
    Mueller, Daniel
    Guenee, Laure
    Alexakis, Alexandre
    ORGANIC LETTERS, 2012, 14 (23) : 5880 - 5883