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

Xiaoji Wang; Yi Zhou; Hesheng Xiao; Wentao Ou; Yiying Pang; Wang Li; Liping Wang; Shuangping Huang

doi:10.1055/s-0040-1707883

Synlett, Table of Contents

Synlett 2020; 31(14): 1404-1408
DOI: 10.1055/s-0040-1707883

letter

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

Xiaoji Wang∗

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China

^cEngineering 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

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China

,

Hesheng Xiao

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China

,

Wentao Ou

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China

,

Yiying Pang

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China

,

Wang Li

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China

,

Liping Wang∗

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China

,

Shuangping Huang∗

^bCollege of Biomedical Engineering, Taiyuan University of Technology, Taiyuan 030024, P. R. of China

› Author Affiliations

Abstract

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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

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References

References and Notes

For general reviews and selected Conia-ene reactions, see:

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