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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 2: 726 - 730

DOI: https://doi.org/10.6023/cjoc202008001

Article

Synthesis of the ABC Ring System of Wallichanol Natural Product

  • Gang Yang ,
  • Xiangyu Feng ,
  • Congcong Han ,
  • Yang Chen ,
  • Shuzhong He
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  • a School of Pharmaceutical Sciences, Guizhou University, Guiyang 550025
    b Guizhou Engineering Laboratory for Synthetic Drugs, Guiyang 550025
    c State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received date: 2020-08-01

  Revised date: 2020-09-17

  Online published: 2020-10-12

Supported by

the National Natural Science Foundation of China(21562011); the National Natural Science Foundation of China(21861010); the Science and Technology Foundation of Guizhou Province([2015]2047); the Science and Technology Foundation of Guizhou Province([2020]1Y108); the Science and Technology Foundation of Guizhou Province([2018]5781); the Case Base Construction Project for Guizhou Graduate Education(KCALK2017012); the Guizhou University Talent Project([2014]36)

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Abstract

A rapid construction of the ABC ring of wallichanol is described. The synthesis features an efficient Diels-Alder reaction for the bicyclo[2.2.2]octane synthesis and a gold-catalyzed alkyne carbometalation for the cyclobutane synthesis. The overall yield of this 7-stepped synthesis is 42%. This strategy can pave the road towards the total synthesis of wallichanol.

Key words： wallichanol; Diels-Alder reaction; carbometalation; total synthesis

Cite this article

Gang Yang , Xiangyu Feng , Congcong Han , Yang Chen , Shuzhong He . Synthesis of the ABC Ring System of Wallichanol Natural Product[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 726 -730 . DOI: 10.6023/cjoc202008001

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