Improved Synthetic Route to
C-Ring Ester-Functionalized Prodigiosenes

Md. Imam Uddin; Srinath Thirumalairajan; Sarah M. Crawford; T. Stanley Cameron; Alison Thompson

doi:10.1055/s-0030-1258769

LETTER

Improved Synthetic Route to C-Ring Ester-Functionalized Prodigiosenes

Md. Imam Uddin, Srinath Thirumalairajan, Sarah M. Crawford*, T. Stanley Cameron, Alison Thompson*
Department of Chemistry, Dalhousie University, Halifax, NS, B3H 4J3, Canada
Fax: +1(902)4941310; e-Mail: Sarah.Crawford@dal.ca; e-Mail: Alison.Thompson@dal.ca;

Abstract

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Abstract

An efficient, optimized, and scalable process for the synthesis of C-ring ester-functionalized prodigiosenes has been developed by (i) exploiting a silylative Mukaiyama aldol strategy for the condensation of alkyl 5-formyl-2,4-dimethylpyrrole-3-carboxylate and 4-methoxy-3-pyrrolin-2-one to form the corresponding ester-functionalized dipyrrinone analogues, and (ii) developing a facile synthesis of stable bromodipyrrin analogues for the use in formal Suzuki coupling reactions. The process was applied to the synthesis of three C-ring ester-functionalized prodigiosenes in multigram scales (up to 6.5 g prodigiosene free-base) with useful yields (35-56% overall yields over three steps starting from the 2-formyl pyrroles).

Key words

prodigiosin - prodigiosene - bromodipyrrin - dipyrrinone - bromination

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