Literature DB >> 23153381

Synthesis of a potent antimalarial amphilectene.

Sergey V Pronin1, Ryan A Shenvi.   

Abstract

7-Isocyano-11(20),14-epiamphilectadiene, the most potent of antimalarial amphilectenes, is synthesized in seven steps from readily available materials. The synthesis is enabled by a new dendrimeric triene (Danishefsky [3]-dendralene) and a new method for stereo- and chemoselective isocyanation. This chemistry provides a useful entry into an underexplored yet promising family of antimalarial terpenoids.

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Year:  2012        PMID： 23153381     DOI： 10.1021/ja310129b

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


  14 in total

1.  Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines.

Authors:  Sergey V Pronin; Christopher A Reiher; Ryan A Shenvi
Journal:  Nature       Date:  2013-09-12       Impact factor: 49.962

2.  Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class.

Authors:  Hai-Hua Lu; Sergey V Pronin; Yevgeniya Antonova-Koch; Stephan Meister; Elizabeth A Winzeler; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2016-05-31       Impact factor: 15.419

3.  Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol.

Authors:  Steven W M Crossley; Ruben M Martinez; Sebastián Guevara-Zuluaga; Ryan A Shenvi
Journal:  Org Lett       Date:  2016-05-13       Impact factor: 6.005

4.  Stereocontrolled Synthesis of Kalihinol C.

Authors:  Christopher A Reiher; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2017-03-02       Impact factor: 15.419

5.  Concise Synthesis of the Antiplasmodial Isocyanoterpene 7,20-Diisocyanoadociane.

Authors:  Alexander S Karns; Bryan D Ellis; Philipp C Roosen; Zeinab Chahine; Karine G Le Roch; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-27       Impact factor: 15.336

Review 6.  Syntheses and biological studies of marine terpenoids derived from inorganic cyanide.

Authors:  Martin J Schnermann; Ryan A Shenvi
Journal:  Nat Prod Rep       Date:  2015-04       Impact factor: 13.423

7.  Broadly Applicable Stereoselective Syntheses of Serrulatane, Amphilectane Diterpenes, and Their Diastereoisomeric Congeners Using Asymmetric Hydrovinylation for Absolute Stereochemical Control.

Authors:  Srinivasarao Tenneti; Souvagya Biswas; Glen Adam Cox; Daniel J Mans; Hwan Jung Lim; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2018-07-27       Impact factor: 15.419

8.  Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications.

Authors:  Justin E Sears; Dale L Boger
Journal:  Acc Chem Res       Date:  2016-01-27       Impact factor: 22.384

9.  Synthesis of medicinally relevant terpenes: reducing the cost and time of drug discovery.

Authors:  Daniel J Jansen; Ryan A Shenvi
Journal:  Future Med Chem       Date:  2014-06       Impact factor: 3.808

Review 10.  Stereospecific nucleophilic substitution at tertiary and quaternary stereocentres.

Authors:  Veeranjaneyulu Lanke; Ilan Marek
Journal:  Chem Sci       Date:  2020-07-28       Impact factor: 9.825
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