Literature DB >> 26371964

Enantioselective Total Synthesis of (-)-Incarviatone A.

Benke Hong1,2, Chao Li1, Zhen Wang3, Jie Chen2, Houhua Li3, Xiaoguang Lei1,3.   

Abstract

We report herein the first total synthesis of (-)-incarviatone A (1) in 14 steps starting from commercially available inexpensive phenylacetic acid (9). Our early stage synthesis relies on the scalable and sequential C-H functionalization to rapidly assemble the indanyl dialdehyde framework. Further biomimetic cascade strategy allows us to obtain the natural product in a one-pot operation. We also conduct detailed mechanistic studies and disclose all the possible intermediates and isomers formed during the biomimetic cascade process.

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Year:  2015        PMID: 26371964     DOI: 10.1021/jacs.5b08551

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


  9 in total

1.  Enantioselective Synthesis of Indolines, Benzodihydrothiophenes, and Indanes by C-H Insertion of Donor/Donor Carbenes.

Authors:  Lucas W Souza; Richard A Squitieri; Christine A Dimirjian; Blanka M Hodur; Leslie A Nickerson; Corinne N Penrod; Jesus Cordova; James C Fettinger; Jared T Shaw
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-18       Impact factor: 15.336

2.  Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C-O Bond Formation under Mild Conditions.

Authors:  Joseph Alvarado; Jeremy Fournier; Armen Zakarian
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-18       Impact factor: 15.336

Review 3.  Synthesis of Natural Products by C-H Functionalization of Heterocycless.

Authors:  Yang Zhang; Michal Szostak
Journal:  Chemistry       Date:  2022-02-17       Impact factor: 5.020

4.  11-Step and Scalable Total Synthesis of Hamigeran M Enabled by Five C-H Functionalizations.

Authors:  Baiyang Jiang; Mingji Dai
Journal:  J Am Chem Soc       Date:  2021-11-23       Impact factor: 16.383

5.  From Pd(OAc)2 to Chiral Catalysts: The Discovery and Development of Bifunctional Mono-N-Protected Amino Acid Ligands for Diverse C-H Functionalization Reactions.

Authors:  Qian Shao; Kevin Wu; Zhe Zhuang; Shaoqun Qian; Jin-Quan Yu
Journal:  Acc Chem Res       Date:  2020-03-31       Impact factor: 22.384

6.  Synthesis of the 8,19-Epoxysteroid Eurysterol A.

Authors:  Ömer Taspinar; Tobias Wilczek; Julian Erver; Martin Breugst; Jörg-Martin Neudörfl; Hans-Günther Schmalz
Journal:  Chemistry       Date:  2020-03-09       Impact factor: 5.236

7.  Chrysomycin A Derivatives for the Treatment of Multi-Drug-Resistant Tuberculosis.

Authors:  Fan Wu; Jing Zhang; Fuhang Song; Sanshan Wang; Hui Guo; Qi Wei; Huanqin Dai; Xiangyin Chen; Xuekui Xia; Xueting Liu; Lixin Zhang; Jin-Quan Yu; Xiaoguang Lei
Journal:  ACS Cent Sci       Date:  2020-05-04       Impact factor: 14.553

Review 8.  Pd-catalysed C-H functionalisation of free carboxylic acids.

Authors:  Suparna Dutta; Trisha Bhattacharya; Finn J Geffers; Marcel Bürger; Debabrata Maiti; Daniel B Werz
Journal:  Chem Sci       Date:  2022-01-10       Impact factor: 9.825

9.  Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C-H/C-H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F.

Authors:  Zhe Zhuang; Alastair N Herron; Shuang Liu; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2021-01-04       Impact factor: 15.419

  9 in total

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