ArticleThe Journal of organic chemistry2011
Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.
Article in The Journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 57 citations in OpenAlex.
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- Design of Iodonium Salts for UV or Near-UV LEDs for Photoacid Generator and Polymerization Purposes.Molecules (Basel, Switzerland) · 2019Article
- Synthetic studies towards the penicisulfuranols: Synthesis of an advanced spirocyclic diketopiperazine intermediate.Tetrahedron · 2019Article
- Convergent synthesis and structural confirmation of phellodonin and sarcodonin ε.Organic letters · 2013Article
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Authors and funding
5 authors at 1 institution in 1 country.
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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 1β-2β position of 1a to the 2β-3β 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 α-oxidation of hydroxamic acids to aminals.
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