Al-catalyzed facile construction of quaternary C-C bonds by the allylic substitution of tertiary alcohols: a concise and formal synthesis of (±)-mersicarpine.
ABSTRACT In close quarters: A concise, high-yielding, and more sustainable route for the synthesis of (±)-mersicarpine in nine linear steps from commercially available indole and succinic anhydride is presented. It is also demonstrated that the novel protocol can be commonly used for the rapid and flexible construction of a diverse class of mersicarpine analogues.
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ABSTRACT: The formal syntheses of N-methylwelwitindolinone C isothiocyanate (4) and several other welwitindolinones 5-8 were achieved by the independent synthesis of 79. The synthesis featured a Lewis acid-mediated coupling between a heteroaryl carbinol and bis-TMS enol ether, an intramolecular enolate arylation, and an unprecedented intramolecular allylic alkylation of a γ-acyloxyenone.Tetrahedron 07/2013; 69(27-28):5588-5603. · 2.80 Impact Factor