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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 6: 1571 - 1577

DOI: https://doi.org/10.6023/cjoc202001031

Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol

  • Han Jilai ,
  • Tang Meilin ,
  • Sun Xun
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  • a Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai 201203;
    b The Institutes of Integrative Medicine of Fudan University, Shanghai 200040;
    c Institutes of Biomedical Sciences, Fudan University, Shanghai 200433

Received date: 2020-01-23

  Revised date: 2020-03-13

  Online published: 2020-04-10

Supported by

Project supported by the National Natural Science Foundation of China (No. 81673297), the Shanghai Committee of Science and Technology (No. 17431902500), and the China Postdoctoral Science Foundation (No. 2019M651384).

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Abstract

This paper has focused on developing a novel methodology for the total synthesis of quadrangularin A (3) and pallidol (4). These two resveratrol dimers have been obtained from the inexpensive materials of 3,5-dimethoxybenzaldehyde (5) and 3,5-dimethoxybenzaldehyde (6) within 9 steps and 11 steps with total yields of 2.6% and 1.3%, respectively. The stilbene skeleton constructed by two symmetric or asymmetric aromatic rings (A and B) has been synthesized simply through Knoevenagel reaction under mild conditions with yield of more than 98%, which expanded the diversity of stilbene skeleton (7), and addressed the problems of limited expansion of asymmetric structure, low yield and complex operation. In addition, the key intermediate of 4-enaldehyde skeleton structure (9) could be used to construct aromatic rings of C and D efficiently, which has thrown light on the expansion of resveratrol dimers with aromatic ring A, B, C and D in diversity structure. All the intermediates and natural products have been characterized by 1H NMR, 13C NMR, and HRMS.

Key words： resveratrol oligomer; Friedel-Crafts reaction; Grignard regent addition reaction; total synthesis

Cite this article

Han Jilai , Tang Meilin , Sun Xun . Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1571 -1577 . DOI: 10.6023/cjoc202001031

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