Total Synthesis of (-)-Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p-Quinone

Yang Long; Yiming Ding; Hai Wu; Chunlei Qu; Hong Liang; Min Zhang; Xiaoli Zhao; Xianwen Long; Shu Wang; Pema-Tenzin Puno; Jun Deng

doi:10.1002/anie.201911978

Total Synthesis of (-)-Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p-Quinone

Angew Chem Int Ed Engl. 2019 Dec 2;58(49):17552-17557. doi: 10.1002/anie.201911978. Epub 2019 Nov 8.

Authors

Yang Long^{1

2}, Yiming Ding^{2

3}, Hai Wu^{2

3}, Chunlei Qu^{2

3}, Hong Liang^{2

3}, Min Zhang^{2

3}, Xiaoli Zhao^{2

3}, Xianwen Long^{2

3}, Shu Wang¹, Pema-Tenzin Puno², Jun Deng²

Affiliations

¹ Department of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, 132 Lanhei Road, Kunming, China.
³ University of Chinese Academy of Sciences, Beijing, 100049, China.

PMID: 31608523
DOI: 10.1002/anie.201911978

Abstract

The first copper-catalyzed intermolecular [5+2] homodimerization of hydroxy p-quinone is presented, furnishing bicyclo[3.2.1]octadienone core structures in typically good yields and excellent diastereoselectivities. Applying this synthetic approach enables a concise nine-step total synthesis of (-)-perezoperezone from commercially available 3,5-dimethoxytoluene.

Keywords: 5+2 cycloaddition; dimerization; natural products; perezoperezone; total synthesis.

Publication types

Research Support, Non-U.S. Gov't

Abstract

Publication types

Grants and funding