11-Step Total Synthesis of Araiosamines

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[1] Tian, Maoqun
[2] Yan, Ming
[3] Baran, Phil S.
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Baran, Phil S. (pbaran@scripps.edu) | 1600年 / American Chemical Society卷 / 138期
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A concise route to a small family of exotic marine alkaloids known as the araiosamines has been developed; and their absolute configuration has been assigned. The dense array of functionality; high polarity; and rich stereochemistry coupled with equilibrating topologies present an unusual challenge for chemical synthesis and an opportunity for innovation. Key steps involve the use of a new reagent for guanidine installation; a remarkably selective C-H functionalization; and a surprisingly simple final step that intersects a presumed biosynthetic intermediate. Synthetic araiosamines were shown to exhibit potency against Gram-positive and -negative bacteria despite a contrary report of no activity. © 2016 American Chemical Society;
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