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Efficient total synthesis of ammosamide B.

ABSTRACT: A total synthesis of ammosamide B, a metabolite of the marine-derived Streptomyces strain CNR-698, has been executed in nine steps and 6.9% overall yield. The key step involves the condensation of a 4,6-diBoc-protected 1,3,4,6-tetraaminobenzene derivative with dimethyl 2-ketoglutaconate, which effectively constructs the pyrrolidinone ring and the quinoline ring in a single step. This contributes a unique approach to the synthesis of pyrroloquinoline alkaloids that offers the advantages of brevity and relatively high overall yield.

SUBMITTER: Reddy PV

PROVIDER: S-EPMC2894265 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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Efficient total synthesis of ammosamide B.

Reddy P V Narasimha PV Banerjee Biplab B Cushman Mark M

Organic letters 20100701 13

A total synthesis of ammosamide B, a metabolite of the marine-derived Streptomyces strain CNR-698, has been executed in nine steps and 6.9% overall yield. The key step involves the condensation of a 4,6-diBoc-protected 1,3,4,6-tetraaminobenzene derivative with dimethyl 2-ketoglutaconate, which effectively constructs the pyrrolidinone ring and the quinoline ring in a single step. This contributes a unique approach to the synthesis of pyrroloquinoline alkaloids that offers the advantages of brevit ...[more]

PMID: 20515072

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