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Biomimetic total synthesis of malbrancheamide and malbrancheamide B.

ABSTRACT: The biomimetic total syntheses of both malbrancheamide and malbrancheamide B are reported. The synthesis of the two monochloro species enabled the structure of malbrancheamide B to be unambiguously assigned. The syntheses each feature an intramolecular Diels-Alder reaction of a 5-hydroxypyrazin-2(1H)-one to construct the bicyclo[2.2.2]diazaoctane core, which has also been proposed as the biosynthetic route to these compounds.

SUBMITTER: Miller KA

PROVIDER: S-EPMC2837585 | biostudies-literature | 2008 Apr

REPOSITORIES: biostudies-literature

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Biomimetic total synthesis of malbrancheamide and malbrancheamide B.

Miller Kenneth A KA Welch Timothy R TR Greshock Thomas J TJ Ding Yousong Y Sherman David H DH Williams Robert M RM

The Journal of organic chemistry 20080318 8

The biomimetic total syntheses of both malbrancheamide and malbrancheamide B are reported. The synthesis of the two monochloro species enabled the structure of malbrancheamide B to be unambiguously assigned. The syntheses each feature an intramolecular Diels-Alder reaction of a 5-hydroxypyrazin-2(1H)-one to construct the bicyclo[2.2.2]diazaoctane core, which has also been proposed as the biosynthetic route to these compounds. ...[more]

PMID: 18345688

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