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Scope and Mechanism of Direct Indole and Pyrrole Couplings Adjacent to Carbonyl Compounds: Total Synthesis of Acremoauxin A and Oxazinin 3

Scope and Mechanism of Direct Indole and Pyrrole Couplings Adjacent to Carbonyl Compounds: Total Synthesis of Acremoauxin A and Oxazinin 3

Jeremy M Richter, Brandon W Whitefield, Thomas J Maimone, David W Lin, M Pilar Castroviejo, Phil S Baran

J Am Chem Soc. 2007 Oct 24;129(42):12857-69.

PMID: 17900115

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP113502526	Ketorolac Related Compound C		113502-52-6	Price

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