1264728-77-9Relevant articles and documents
Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family
Lin, David W.,Masuda, Takeshi,Biskup, Moritz B.,Nelson, Jonathan D.,Baran, Phil S.
, p. 1013 - 1030 (2011/04/15)
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.
