Literature DB >> 21861520

Total syntheses of drimane-type sesquiterpenoids enabled by a gold-catalyzed tandem reaction.

Hang Shi1, Lichao Fang, Ceheng Tan, Lili Shi, Weibin Zhang, Chuang-chuang Li, Tuoping Luo, Zhen Yang.   

Abstract

Development of a gold-catalyzed tandem reaction of 1,7-diynes with both internal and external nucleophiles was realized, which constructed five chemical bonds, two rings, and two stereogenic centers in a single step. Based on the novel cascade transformation, we achieved a unified strategy toward the stereoselective total syntheses of C-15 oxygenated drimane-type sesquiterpenoids and their analogues, which provided the natural products kuehneromycin A, antrocin, anhydromarasmone, and marasmene as a proof-of-concept study.

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Year:  2011        PMID： 21861520     DOI： 10.1021/ja206837j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  Light-Driven Intermolecular Charge Transfer Induced Reactivity of Ethynylbenziodoxol(on)e and Phenols.

Authors:  Bin Liu; Chern-Hooi Lim; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2018-10-02       Impact factor: 15.419

2.  Total Syntheses of the Reported Structures of Curcusones I and J through Tandem Gold Catalysis.

Authors:  Yong Li; Mingji Dai
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

3.  Catalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones.

Authors:  Xinpei Cai; Weida Liang; Mingxin Liu; Xiating Li; Mingji Dai
Journal:  J Am Chem Soc       Date:  2020-07-27       Impact factor: 15.419

4.  Mechanistic elucidation of the tandem Diels-Alder/(3 + 2) cycloadditions in the design and syntheses of heterosteroids.

Authors:  Benedicta Donkor; Abdul Rashid Umar; Ernest Opoku
Journal:  J Mol Model       Date:  2022-02-27       Impact factor: 1.810

5.  Selective syntheses of Δ(α,β) and Δ(β,γ) butenolides from allylic cyclopropenecarboxylates via tandem ring expansion/[3,3]-sigmatropic rearrangements.

Authors:  Xiaocong Xie; Yi Li; Joseph M Fox
Journal:  Org Lett       Date:  2013-03-20       Impact factor: 6.005

6.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

7.  Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.

Authors:  Yang Yang; Yu Bai; Siyuan Sun; Mingji Dai
Journal:  Org Lett       Date:  2014-11-20       Impact factor: 6.005

8.  Gold-Catalyzed Hydroalkoxylation/Povarov Reaction Cascade of Alkynols with N-Aryl Imines: Synthesis of Tetrahydroquinolines.

Authors:  Ciwang He; Ju Cai; Yang Zheng; Chao Pei; Lihua Qiu; Xinfang Xu
Journal:  ACS Omega       Date:  2019-09-09

9.  Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes.

Authors:  Mingyue Wu; Zhaobin Han; Huanzhen Ni; Nengzhong Wang; Kuiling Ding; Yixin Lu
Journal:  Chem Sci       Date:  2022-02-11       Impact factor: 9.825

10.  Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes via a gold-catalysed cascade reaction.

Authors:  Junkai Fu; Yueqing Gu; Hao Yuan; Tuoping Luo; Song Liu; Yu Lan; Jianxian Gong; Zhen Yang
Journal:  Nat Commun       Date:  2015-10-16       Impact factor: 14.919
  10 in total

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