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Synlett 2020; 31(14): 1404-1408
DOI: 10.1055/s-0040-1707883
letter
© Georg Thieme Verlag Stuttgart · New York

Formal Synthesis of (±)-Aplykurodinone-1 Based on the Indium-Catalyzed Conia-Ene Reaction

Xiaoji Wang∗
a   School of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China
c   Engineering Research Center of Health Food Design and Nutrition Regulation, School of Chemical Engineering and Energy Technology, Dongguan University of Technology, P. R. of China   Email: 2012207455@tju.edu.cn
,
Yi Zhou
a   School of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China
,
Hesheng Xiao
a   School of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China
,
Wentao Ou
a   School of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China
,
Yiying Pang
a   School of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China
,
Wang Li
a   School of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China
,
Liping Wang∗
a   School of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China
,
Shuangping Huang∗
b   College of Biomedical Engineering, Taiyuan University of Technology, Taiyuan 030024, P. R. of China
› Author AffiliationsWe acknowledge financial support from the National Science Foundation of China (21062088, 21562020) and the Science and Technology Plan Project of Jiangxi Province (No. 20151BBG70028, 20142BBE50006).
Further Information

Publication History

Received: 07 February 2020

Accepted after revision: 25 May 2020

Publication Date:
18 June 2020 (online)

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Abstract

A concise formal synthesis of (±)-aplykurodinone-1 starting from a commercially available material and based on the indium-catalyzed Conia-ene reaction has been accomplished. The synthesis features a Riley selenium dioxide oxidation, a Krapcho dealkoxycarbonylation, and a ring-closing metathesis approach. The synthetic strategy was also supported by a Saegusa oxidation and a classic Michael 1,4-conjugate addition.

Key words

formal synthesis - aplykurodinone-1 - Conia-ene reaction - Riley oxidation - ring-closing metathesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707883.
  • Supporting Information
 

  • References and Notes


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