Literature DB >> 24795487

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.

John T Gupton1, Nakul Telang1, Michael Wormald1, Kristin Lescalleet1, Jon Patteson1, Will Curry1, Andrew Harrison1, Megan Hoerrner1, John Sobieski1, Michael Kimmel1, Emily Kluball1, Thomas Perry1.   

Abstract

A new pyrrole building block is described, which allows for the regiospecific synthesis of 2,3,5-trisubstituted pyrroles and 2,3,4,5- tetrasubstituted pyrroles. Optimization studies are presented for the preparation of the pyrrole building block along with the evaluation of various cross-coupling conditions and cross-coupling agents. A short, formal synthesis of the natural products Polycitone A, Polycitone B and Polycitrin A from the pyrrole building block is also described.

Entities:  

Keywords:  Marine Natural Products; Pyrrole; Suzuki Cross-Coupling; Vilsmeier Formylation

Year:  2014        PMID： 24795487      PMCID： PMC4004070          DOI： 10.1016/j.tet.2014.02.091

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


  7 in total

1.  Modular total synthesis of lamellarin D.

Authors:  Daniel Pla; Antonio Marchal; Christian A Olsen; Fernando Albericio; Mercedes Alvarez
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

2.  Polycitone B and prepolycitrin A: two novel alkaloids from the marine ascidian Polycitor africanus.

Authors:  A Rudi; T Evan; M Aknin; Y Kashman
Journal:  J Nat Prod       Date:  2000-06       Impact factor: 4.050

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

Authors:  John T Gupton; 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
Journal:  Tetrahedron       Date:  2009-05-30       Impact factor: 2.457

4.  Total syntheses of the marine pyrrole alkaloids polycitone A and B.

Authors:  Andreas T Kreipl; Caroline Reid; Wolfgang Steglich
Journal:  Org Lett       Date:  2002-09-19       Impact factor: 6.005

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

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

7.  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
  7 in total
  2 in total

1.  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

2.  Ortho group activation of a bromopyrrole ester in Suzuki-Miyaura cross-coupling reactions: Application to the synthesis of new microtubule depolymerizing agents with potent cytotoxic activities.

Authors:  John T Gupton; Scott Yeudall; Nakul Telang; Megan Hoerrner; Ellis Huff; Evan Crawford; Katie Lounsbury; Michael Kimmel; William Curry; Andrew Harrison; Wen Juekun; Alex Shimozono; Joe Ortolani; Kristin Lescalleet; Jon Patteson; Veronica Moore-Stoll; Cristina C Rohena; Susan L Mooberry; Ahmad J Obaidullah; Glen E Kellogg; James A Sikorski
Journal:  Bioorg Med Chem       Date:  2017-04-11       Impact factor: 3.641
  2 in total

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