Literature DB >> 20161334

The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine akaloids lamellarin G trimethyl ether and ningalin B.

John T Gupton1, Benjamin C Giglio, James E Eaton, Elizabeth A Rieck, Kristin L Smith, Matthew J Keough, Peter J Barelli, Lauren T Firich, Jonathan E Hempel, Timothy M Smith, Rene P F Kanters.   

Abstract

Studies directed at the synthesis of lamellarin G trimethyl ether and ningalin B via vinylogous iminium salt derivatives are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 1,2,3,4-tetrasubstituted pyrrole from a vinylogous iminium salt or vinylogous iminium salt derivative. Subsequent transformations of these highly substituted pyrroles lead to efficient and regiocontrolled formal syntheses of the respective pyrrole containing natural products.

Entities:  

Year:  2009        PMID: 20161334      PMCID: PMC2678759          DOI: 10.1016/j.tet.2009.03.085

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  11 in total

1.  Synthesis and structure-activity relationship study of potent cytotoxic analogues of the marine alkaloid Lamellarin D.

Authors:  Daniel Pla; Antonio Marchal; Christian A Olsen; Andrés Francesch; Carmen Cuevas; Fernando Albericio; Mercedes Alvarez
Journal:  J Med Chem       Date:  2006-06-01       Impact factor: 7.446

2.  Lamellarin alpha 20-sulfate, an inhibitor of HIV-1 integrase active against HIV-1 virus in cell culture.

Authors:  M V Reddy; M R Rao; D Rhodes; M S Hansen; K Rubins; F D Bushman; Y Venkateswarlu; D J Faulkner
Journal:  J Med Chem       Date:  1999-06-03       Impact factor: 7.446

3.  Total synthesis of ningalin B utilizing a heterocyclic azadiene Diels-Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents.

Authors:  D L Boger; D R Soenen; C W Boyce; M P Hedrick; Q Jin
Journal:  J Org Chem       Date:  2000-04-21       Impact factor: 4.354

Review 4.  Recent advances in lamellarin alkaloids: isolation, synthesis and activity.

Authors:  D Pla; F Albericio; M Alvarez
Journal:  Anticancer Agents Med Chem       Date:  2008-10       Impact factor: 2.505

5.  The Application of Vinylogous Iminium Salt Derivatives and Microwave Accelerated Vilsmeier-Haack Reactions to Efficient Relay Syntheses of the Polycitone and Storniamide Natural Products.

Authors:  John T Gupton; Edith J Banner; Melissa D Sartin; Matthew B Coppock; Jonathan E Hempel; Anastasia Kharlamova; Daniel C Fisher; Ben C Giglio; Kristin L Smith; Matt J Keough; Timothy M Smith; Rene P F Kanters; Raymond N Dominey; James A Sikorski
Journal:  Tetrahedron       Date:  2008       Impact factor: 2.457

Review 6.  Lamellarins and related pyrrole-derived alkaloids from marine organisms.

Authors:  Hui Fan; Jiangnan Peng; Mark T Hamann; Jin-Feng Hu
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

Review 7.  Lamellarins, from A to Z: a family of anticancer marine pyrrole alkaloids.

Authors:  Christian Bailly
Journal:  Curr Med Chem Anticancer Agents       Date:  2004-07

8.  Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated alpha-aminonitrile.

Authors:  Johannes C Liermann; Till Opatz
Journal:  J Org Chem       Date:  2008-05-24       Impact factor: 4.354

9.  A modular synthesis of the lamellarins: total synthesis of lamellarin G trimethyl ether.

Authors:  Scott T Handy; Yanan Zhang; Howard Bregman
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354

10.  Docking and hydropathic scoring of polysubstituted pyrrole compounds with antitubulin activity.

Authors:  Ashutosh Tripathi; Micaela Fornabaio; Glen E Kellogg; John T Gupton; David A Gewirtz; W Andrew Yeudall; Nina E Vega; Susan L Mooberry
Journal:  Bioorg Med Chem       Date:  2007-12-04       Impact factor: 3.641

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  7 in total

1.  Formyl Group Activation of a Bromopyrrole Ester in Suzuki Cross-Coupling Reactions: Application to a Formal Synthesis of Polycitone A and B and Polycitrin A.

Authors:  John T Gupton; Nakul Telang; Michael Wormald; Kristin Lescalleet; Jon Patteson; Will Curry; Andrew Harrison; Megan Hoerrner; John Sobieski; Michael Kimmel; Emily Kluball; Thomas Perry
Journal:  Tetrahedron       Date:  2014-04-01       Impact factor: 2.457

2.  The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether.

Authors:  John T Gupton; Nakul Telang; Jon Patteson; Kristin Lescalleet; Scott Yeudall; John Sobieski; Andrew Harrison; Will Curry
Journal:  Tetrahedron       Date:  2014-12-30       Impact factor: 2.457

3.  The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones.

Authors:  John T Gupton; Nakul Telang; Edith J Banner; Emily J Kluball; Kayleigh E Hall; Kara L Finzel; Xin Jia; Spencer R Bates; R Scott Welden; Benjamin C Giglio; James E Eaton; Peter J Barelli; Lauren T Firich; John A Stafford; Matthew B Coppock; Eric F Worrall; Rene P F Kanters; Kerry Keertikar; Rebecca Osterman
Journal:  Tetrahedron       Date:  2010-11-20       Impact factor: 2.457

4.  Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine.

Authors:  Susanna K Maisto; Angela P Leersnyder; Gwyneth L Pudner; Jonathan R Scheerer
Journal:  J Org Chem       Date:  2020-06-30       Impact factor: 4.354

5.  Further studies on the application of vinylogous amides and β-halovinylaldehydes to the regiospecific synthesis of unsymmetrical, polyfunctionalized 2,3,4- and 1,2,3,4- substituted pyrroles.

Authors:  John T Gupton; Alex Shimozono; Evan Crawford; Joe Ortolani; Evan Clark; Matt Mahoney; Campbell Heese; Jeffrey Noble; Carlos Perez Mandry; Rene Kanters; Raymond N Dominey; Emma W Goldman; James A Sikorski; Daniel C Fisher
Journal:  Tetrahedron       Date:  2018-04-07       Impact factor: 2.457

Review 6.  Anticancer properties of lamellarins.

Authors:  Christian Bailly
Journal:  Mar Drugs       Date:  2015-02-19       Impact factor: 5.118

Review 7.  Synthetic approaches to the lamellarins--a comprehensive review.

Authors:  Dennis Imbri; Johannes Tauber; Till Opatz
Journal:  Mar Drugs       Date:  2014-12-18       Impact factor: 5.118

  7 in total

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