Literature DB >> 15040738

Total synthesis of (+/-)-kalihinol C.

Ryan D White1, Gregg F Keaney, Corin D Slown, John L Wood.   

Abstract

The total synthesis of kalihinol C, a bis-isonitrile marine diterpenoid isolated from Acanthella sp., is reported. The decalin framework was established via an intramolecular Diels-Alder cycloaddition and subsequently functionalized through a series of substrate-controlled diastereoselective transformations to install the tertiary isonitrile, beta-hydroxy isonitrile, and pendant tetrahydrofuranyl ring.

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Year:  2004        PMID： 15040738     DOI： 10.1021/ol049918b

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Identification of the major sex pheromone component of the scale insect, Aulacaspis murrayae Takahashi.

Authors:  Hsiao-Yung Ho; Bowroju Suresh Kuarm; Chi-Hung Ke; Yi-Kai Ma; Han-Jung Lee; Chao-Chih Cheng; Kelvin Kwen Liu; Jocelyn G Millar
Journal:  J Chem Ecol       Date:  2014-04-01       Impact factor: 2.626

2.  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

3.  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

4.  Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination.

Authors:  Kurtis M Carsch; Ida M DiMucci; Diana A Iovan; Alex Li; Shao-Liang Zheng; Charles J Titus; Sang Jun Lee; Kent D Irwin; Dennis Nordlund; Kyle M Lancaster; Theodore A Betley
Journal:  Science       Date:  2019-09-13       Impact factor: 47.728

5.  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

6.  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 7.  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

Review 8.  Marine antimalarials.

Authors:  Ernesto Fattorusso; Orazio Taglialatela-Scafati
Journal:  Mar Drugs       Date:  2009-04-23       Impact factor: 5.118

9.  Synthesis and potent antimalarial activity of kalihinol B.

Authors:  Mary Elisabeth Daub; Jacques Prudhomme; Karine Le Roch; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2015-04-09       Impact factor: 15.419

10.  Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents.

Authors:  Raphael K Klake; Samantha L Gargaro; Skyler L Gentry; Sharon O Elele; Joshua D Sieber
Journal:  Org Lett       Date:  2019-09-18       Impact factor: 6.005
  10 in total

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