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

DW Lin, T Masuda, MB Biskup, JD Nelson…

Index: Lin, David W.; Masuda, Takeshi; Biskup, Moritz B.; Nelson, Jonathan D.; Baran, Phil S. Journal of Organic Chemistry, 2011 , vol. 76, # 4 p. 1013 - 1030

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Citation Number: 28

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 ...