The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids Rigidin and Rigidin E

    Authors

    J. T. Gupton; E. J. Banner; A. B. Scharf; B. K. Norwood; R. P. F. Kanters; R. N. Dominey; J. E. Hempel; A. Kharlamova; I. Bluhn-Chertudi; C. R. Hickenboth; B. A. Little; M. D. Sartin; M. B. Coppock; K. E. Krumpe; B. S. Burnham; H. Holt; K. X. Du; K. M. Keertikar; A. Diebes; S. Ghassemi;J. A. Sikorski

    Comments

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    Abbreviated Journal Title

    Tetrahedron

    Keywords

    vinamidinium salt; pyrrole; marine natural product; microwave; acceleration; MARINE NATURAL-PRODUCTS; RELAY SYNTHESIS; POLYCITONE-A; AMINES; Chemistry, Organic

    Abstract

    Studies directed on the synthesis of the pyrrole containing marine natural products Rigidin and Rigidin E via vinylogous iminium salts are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole from a vinamidinium salt followed by acylation at the 5-position of pyrrole. Halogenation and aminocarbonylation at the 3-position of pyrrole followed by hydrolysis of the ester group at C-2 and subsequent Curtius rearrangement generates the pyrrolopyrimidine skeleton. A final deprotection step completes the synthesis of Rigidin and Rigidin E. (c) 2006 Elsevier Ltd. All rights reserved.

    Journal Title

    Tetrahedron

    Volume

    62

    Issue/Number

    35

    Publication Date

    1-1-2006

    Document Type

    Article

    Language

    English

    First Page

    8243

    Last Page

    8255

    WOS Identifier

    WOS:000239885200002

    ISSN

    0040-4020

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