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Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.

ABSTRACT: A sweeping structural revision of the sarcodonin natural product family (published structures 1a-13a) is proposed after extensive studies aimed at their chemical synthesis. Key features of revised structure 1b include replacement of the N,N-dioxide moiety with an oxime, ring-opening of the central diketopiperazine, and transposition of the terphenyl wing from the 1?-2? position of 1a to the 2?-3? position of 1b. This structure revision arose from the serendipitous synthesis of a benzodioxane aminal (44) whose structure was unambiguously determined by X-ray crystallography and whose spectral properties bore considerable resemblance to the published data for the sarcodonins. A versatile new method for O-arylation of hydroxamic acids is also reported herein, as well as a manganese(III)-mediated ?-oxidation of hydroxamic acids to aminals.

SUBMITTER: Lin DW

PROVIDER: S-EPMC3089814 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.

Lin David W DW Masuda Takeshi T Biskup Moritz B MB Nelson Jonathan D JD Baran Phil S PS

The Journal of organic chemistry 20110120 4

A sweeping structural revision of the sarcodonin natural product family (published structures 1a-13a) is proposed after extensive studies aimed at their chemical synthesis. Key features of revised structure 1b include replacement of the N,N-dioxide moiety with an oxime, ring-opening of the central diketopiperazine, and transposition of the terphenyl wing from the 1β-2β position of 1a to the 2β-3β position of 1b. This structure revision arose from the serendipitous synthesis of a benzodioxane ami ...[more]

PMID: 21250718

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