Literature DB >> 25562696

Concise syntheses of dictyodendrins A and F by a sequential C-H functionalization strategy.

Atsushi D Yamaguchi1, Kathryn M Chepiga, Junichiro Yamaguchi, Kenichiro Itami, Huw M L Davies.   

Abstract

Syntheses of dictyodendrins A and F have been achieved using a sequential C-H functionalization strategy. The N-alkylpyrrole core is fully functionalized by means of a rhodium(I)-catalyzed C-H arylation at the C3-position, a rhodium(II)-catalyzed double C-H insertion at the C2- and C5-positions, and a Suzuki-Miyaura cross-coupling reaction at the C4-position. The syntheses of dictyodendrins A and F were completed by formal 6π-electrocyclization to generate the pyrrolo[2,3-c]carbazole core of the natural products.

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Year:  2015        PMID: 25562696     DOI: 10.1021/ja512059d

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


  12 in total

Review 1.  Enzymatic CH functionalizations for natural product synthesis.

Authors:  Fuzhuo Li; Xiao Zhang; Hans Renata
Journal:  Curr Opin Chem Biol       Date:  2018-09-27       Impact factor: 8.822

2.  A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks.

Authors:  Wenhan Zhang; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2016-08-11       Impact factor: 15.419

3.  Site-selective and stereoselective functionalization of non-activated tertiary C-H bonds.

Authors:  Kuangbiao Liao; Thomas C Pickel; Vyacheslav Boyarskikh; John Bacsa; Djamaladdin G Musaev; Huw M L Davies
Journal:  Nature       Date:  2017-11-20       Impact factor: 49.962

4.  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 5.  Advancing the Logic of Chemical Synthesis: C-H Activation as Strategic and Tactical Disconnections for C-C Bond Construction.

Authors:  Nelson Y S Lam; Kevin Wu; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-04       Impact factor: 16.823

6.  The total synthesis of K-252c (staurosporinone) via a sequential C-H functionalisation strategy.

Authors:  J C Fox; R E Gilligan; A K Pitts; H R Bennett; M J Gaunt
Journal:  Chem Sci       Date:  2016-01-21       Impact factor: 9.825

Review 7.  C4-H indole functionalisation: precedent and prospects.

Authors:  Jagadeesh Kalepu; Parthasarathy Gandeepan; Lutz Ackermann; Lukasz T Pilarski
Journal:  Chem Sci       Date:  2018-04-20       Impact factor: 9.825

Review 8.  Collective Approach to Advancing C-H Functionalization.

Authors:  Huw M L Davies; Daniel Morton
Journal:  ACS Cent Sci       Date:  2017-09-11       Impact factor: 14.553

9.  C-H arylation and alkenylation of imidazoles by nickel catalysis: solvent-accelerated imidazole C-H activation.

Authors:  Kei Muto; Taito Hatakeyama; Junichiro Yamaguchi; Kenichiro Itami
Journal:  Chem Sci       Date:  2015-09-08       Impact factor: 9.825

10.  Pd(ii)-catalyzed remote regiodivergent ortho- and meta-C-H functionalizations of phenylethylamines.

Authors:  Shangda Li; Huafang Ji; Lei Cai; Gang Li
Journal:  Chem Sci       Date:  2015-06-25       Impact factor: 9.825

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