Literature DB >> 12227770

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

Andreas T Kreipl1, Caroline Reid, Wolfgang Steglich.   

Abstract

Polycitone B (2) was obtained in four steps from pyrrole dicarboxylic acid 3, including Friedel-Crafts reaction of the corresponding acid chloride with anisole. The conversion of 2 into polycitone A (1) was achieved in two steps via Mitsunobu alkylation of the pyrrolic NH group. The synthesis of polycitone A proceeds in 18% overall yield and offers the possibility of varying the substituents on the pyrrole ring.

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Year:  2002        PMID: 12227770     DOI: 10.1021/ol026555b

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


  6 in total

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Authors:  Jiangnan Peng; Jing Li; Mark T Hamann
Journal:  Alkaloids Chem Biol       Date:  2005

2.  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

Review 3.  Applications of Friedel-Crafts reactions in total synthesis of natural products.

Authors:  Majid M Heravi; Vahideh Zadsirjan; Pegah Saedi; Tayebeh Momeni
Journal:  RSC Adv       Date:  2018-12-03       Impact factor: 4.036

4.  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 5.  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

6.  Modification of marine natural product ningalin B and SAR study lead to potent P-glycoprotein inhibitors.

Authors:  Chao Yang; Iris L K Wong; Wen Bin Jin; Tao Jiang; Larry M C Chow; Sheng Biao Wan
Journal:  Mar Drugs       Date:  2014-10-17       Impact factor: 5.118

  6 in total

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