Literature DB >> 15656618

The total synthesis of gambierol.

Henry W B Johnson1, Utpal Majumder, Jon D Rainier.   

Abstract

This communication describes the total synthesis of the marine polyether toxin, gambierol. This work couples our iterative C-glycoside/enol ether-olefin metathesis strategy to the subunits with a unique olefin metathesis/carbonyl olefination reaction to bring the subunits together.

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Year:  2005        PMID： 15656618     DOI： 10.1021/ja043396d

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


  20 in total

1.  Enol ethers as substrates for efficient Z- and enantioselective ring-opening/cross-metathesis reactions promoted by stereogenic-at-Mo complexes: utility in chemical synthesis and mechanistic attributes.

Authors:  Miao Yu; Ismail Ibrahem; Masayuki Hasegawa; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-24       Impact factor: 15.419

2.  TRPV1 as a key determinant in ciguatera and neurotoxic shellfish poisoning.

Authors:  Eva Cuypers; Angel Yanagihara; Jon D Rainier; Jan Tytgat
Journal:  Biochem Biophys Res Commun       Date:  2007-07-16       Impact factor: 3.575

3.  Harnessing glycal-epoxide rearrangements: the generation of the AB, EF, and IJ rings of adriatoxin.

Authors:  Clement Osei Akoto; Jon D Rainier
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 4.  The continuing saga of the marine polyether biotoxins.

Authors:  K C Nicolaou; Michael O Frederick; Robert J Aversa
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Gambierol inhibition of voltage-gated potassium channels augments spontaneous Ca2+ oscillations in cerebrocortical neurons.

Authors:  Zhengyu Cao; Yanjun Cui; Eric Busse; Suneet Mehrotra; Jon D Rainier; Thomas F Murray
Journal:  J Pharmacol Exp Ther       Date:  2014-06-23       Impact factor: 4.030

6.  Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides.

Authors:  Laura Alberch; Gang Cheng; Seung-Kee Seo; Xuehua Li; Fabien P Boulineau; Alexander Wei
Journal:  J Org Chem       Date:  2011-03-18       Impact factor: 4.354

7.  Maitotoxin: An Inspiration for Synthesis.

Authors:  K C Nicolaou; Robert J Aversa
Journal:  Isr J Chem       Date:  2011-04       Impact factor: 3.333

8.  Olefinic-lactone cyclizations to macrocycles.

Authors:  John C Rohanna; Jon D Rainier
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

9.  Two-directional olefinic-ester ring-closing metathesis using reduced Ti alkylidenes. A rapid entry into polycyclic ether skeletons.

Authors:  Yuan Zhang; Jon D Rainier
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

10.  Olefinic-amide and olefinic-lactam cyclizations.

Authors:  Jie Zhou; Jon D Rainier
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005
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