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An approach for the synthesis of nakamuric acid.

ABSTRACT: The biosynthesis of dimeric pyrrole-imidazole alkaloids is likely mediated by enzyme-catalyzed reversible single-electron transfer (SET) cycloaddition. We now show that Ir(ppy)3 can promote SET-mediated formal [2+2] and [4+2] cycloaddition reactions of pyrrole-imidazole alkaloids-related substrates under photolytic conditions. This biomimetic approach is useful for the construction of the core skeleton of nakamuric acid and sceptrin.

SUBMITTER: Wang X

PROVIDER: S-EPMC4430124 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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An approach for the synthesis of nakamuric acid.

Wang Xiaolei X Chen Chuo C

Tetrahedron 20150601 22

The biosynthesis of dimeric pyrrole-imidazole alkaloids is likely mediated by enzyme-catalyzed reversible single-electron transfer (SET) cycloaddition. We now show that Ir(ppy)<sub>3</sub> can promote SET-mediated formal [2+2] and [4+2] cycloaddition reactions of pyrrole-imidazole alkaloids-related substrates under photolytic conditions. This biomimetic approach is useful for the construction of the core skeleton of nakamuric acid and sceptrin. ...[more]

PMID: 25983349

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