725252-07-3Relevant academic research and scientific papers
Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families
Baran, Phil S.,Richter, Jeremy M.
, p. 7450 - 7451 (2004)
The invention of a method for the direct union of indoles and carbonyl compounds (ketones, amides, esters) is described. Using this new method, a short, enantioselective, gram-scale and protecting group-free synthetic entry to the fischerindole and hapali
Addition of indoles to oxyallyl cations for facile access to α-indole carbonyl compounds
Tang, Qiang,Chen, Xingkuan,Tiwari, Bhoopendra,Chi, Yonggui Robin
supporting information; experimental part, p. 1922 - 1925 (2012/06/15)
A direct coupling of unprotected indoles and α-halo ketones via in situ generated oxyallyl cation intermediates is described. The reactions efficiently afford α-indole carbonyl compounds with good to quantitative yields.
Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach
Richter, Jeremy M.,Ishihara, Yoshihiro,Masuda, Takeshi,Whitefield, Brandon W.,Llamas, Tomas,Pohjakallio, Antti,Baran, Phil S.
supporting information; experimental part, p. 17938 - 17954 (2009/07/11)
Full details are provided for the total synthesis of several members of the hapalindole family of natural products, including hapalindole Q, 12-epi-hapalindole D, 12-epi-fischerindole U, 12-epi-fischerindole G, 12-epi-fischerindole I, and welwitindolinone
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.
