125537-93-1Relevant articles and documents
Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: Total synthesis of acremoauxin A and oxazinin 3
Richter, Jeremy M.,Whitefield, Brandon W.,Maimone, Thomas J.,Lin, David W.,Castroviejo, M. Pilar,Baran, Phil S.
, p. 12857 - 12869 (2008/09/16)
Full details are provided for a recently invented method to couple indoles and pyrroles to carbonyl compounds. The reaction is ideally suited for structurally complex substrates and exhibits high levels of chemoselectivity (functional group tolerability), regioselectivity (coupling occurs exclusively at C-3 of indole or C-2 of pyrrole), stereoselectivity (substrate control), and practicality (amenable to scaleup). In addition, quaternary stereocenters are easily and predictably generated. The reaction has been applied to a number of synthetic problems including total syntheses of members of the hapalindole family of natural products, ketorolac, acremoauxin A, and oxazinin 3. Mechanistically, this coupling protocol appears to operate by a single electron-transfer process requiring generation of an electron-deficient radical adjacent to a carbonyl which is then intercepted by an indole or pyrrole anion.
Synthesis of Acremoauxin A, a New Plant Growth Regulator Produced by Acremonium roseum I 4267
Yoshida, Noriyuki,Sassa, Takeshi
, p. 2681 - 2683 (2007/10/02)
Acremoauxin A, a new fungal auxin derivative produced by A. roseum I 4267, was synthesized from indole, lactic acid, and D-mannitol. (+)-2-(3-Indolyl)propionic acid was prepared from its synthetic racemate by biological resolution using the acremoauxin-producing fungus.The synthetically confirmed structure of acremoauxin A was 1-O--D-arabitol (1).