Literature DB >> 19170539

Total synthesis of (+/-)-rhazinal using novel palladium-catalyzed cyclizations.

Alfred L Bowie1, Dirk Trauner.   

Abstract

A concise synthesis of (+/-)-rhazinal that hinges on novel oxidative Heck cyclizations and palladium-catalyzed direct couplings is described. An X-ray structure of N-MOM-rhazinal, which provides insight into the conformation of the strained 9-membered lactam ring, is described.

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Year:  2009        PMID: 19170539     DOI: 10.1021/jo801791j

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  16 in total

1.  Iridium-catalyzed arene ortho-silylation by formal hydroxyl-directed C-H activation.

Authors:  Eric M Simmons; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-11-15       Impact factor: 15.419

2.  Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

Authors:  Keary M Engle; Navid Dastbaravardeh; Peter S Thuy-Boun; Dong-Hui Wang; Aaron C Sather; Jin-Quan Yu
Journal:  Organic Synth       Date:  2015-03-12

3.  Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors:  Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal:  Synthesis (Stuttg)       Date:  2012-05-25       Impact factor: 3.157

4.  Pd(II)-catalyzed hydroxyl-directed C-H olefination enabled by monoprotected amino acid ligands.

Authors:  Yi Lu; Dong-Hui Wang; Keary M Engle; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-04-28       Impact factor: 15.419

5.  Highly convergent total synthesis of (+)-lithospermic acid via a late-stage intermolecular C-H olefination.

Authors:  Dong-Hui Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2011-03-28       Impact factor: 15.419

6.  Ligand-accelerated C-H activation reactions: evidence for a switch of mechanism.

Authors:  Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

7.  Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group.

Authors:  Enver Cagri Izgu; Thomas R Hoye
Journal:  Chem Sci       Date:  2013-02       Impact factor: 9.825

8.  Total synthesis of rhazinilam: axial to point chirality transfer in an enantiospecific Pd-catalyzed transannular cyclization.

Authors:  Zhenhua Gu; Armen Zakarian
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

9.  Biosynthesis of Strained Piperazine Alkaloids: Uncovering the Concise Pathway of Herquline A.

Authors:  Xia Yu; Fang Liu; Yi Zou; Man-Cheng Tang; Leibniz Hang; K N Houk; Yi Tang
Journal:  J Am Chem Soc       Date:  2016-10-06       Impact factor: 15.419

10.  A Robust Protocol for Pd(II)-catalyzed C-3 Arylation of (1H) Indazoles and Pyrazoles: Total Synthesis of Nigellidine Hydrobromide.

Authors:  Mengchun Ye; Andrew J F Edmunds; James A Morris; David Sale; Yejia Zhang; Jin-Quan Yu
Journal:  Chem Sci       Date:  2013-06-01       Impact factor: 9.825

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