Literature DB >> 31608523

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

Yang Long1,2, Yiming Ding2,3, Hai Wu2,3, Chunlei Qu2,3, Hong Liang2,3, Min Zhang2,3, Xiaoli Zhao2,3, Xianwen Long2,3, Shu Wang1, Pema-Tenzin Puno2, Jun Deng2.   

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.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

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

Year:  2019        PMID: 31608523     DOI: 10.1002/anie.201911978

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  1 in total

1.  Fused multicyclic polyketides with a two-spiro-carbon skeleton from mangrove-derived endophytic fungus Epicoccum nigrum SCNU-F0002.

Authors:  Zhangyuan Yan; Jialin Li; Geting Ye; Tao Chen; Meimei Li; Yanmin Liang; Yuhua Long
Journal:  RSC Adv       Date:  2020-08-03       Impact factor: 3.361

  1 in total

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