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Asymmetric total synthesis of ent-cyclooroidin.

ABSTRACT: An enantiospecific total synthesis of the pyrrole-imidazole natural product cyclooroidin from histidine is described. The key N1-C9 bond is constructed through an intramolecular SN2-type of reaction of a chloro ester. Subsequent imidazole azidation at the 2-position, pyrrole bromination, azide reduction, and deprotection leads to the completion of the synthesis.

SUBMITTER: Mukherjee S 

PROVIDER: S-EPMC3099645 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Asymmetric total synthesis of ent-cyclooroidin.

Mukherjee Sabuj S   Sivappa Rasapalli R   Yousufuddin Muhammed M   Lovely Carl J CJ  

Organic letters 20101101 21

An enantiospecific total synthesis of the pyrrole-imidazole natural product cyclooroidin from histidine is described. The key N1-C9 bond is constructed through an intramolecular SN2-type of reaction of a chloro ester. Subsequent imidazole azidation at the 2-position, pyrrole bromination, azide reduction, and deprotection leads to the completion of the synthesis. ...[more]

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