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Title: One-step synthesis of 3-formyl-2-furylcarbinols and elaboration to unprecedented furotropones
Authors: Dhiman, Seema
Ramasastry, S S V
Keywords: Furfuryl alcohols;3-Furancarboxaldehydes;3-Formyl-2-furylcarbinols;Furotropone;Cyclohepta[b]furans;Bismuth chloride;Lithiation;Alkylation;Cyclization
Issue Date: 3-Aug-2013
Abstract: A general and unprecedented strategy for the synthesis of furo[2,3-d]tropone system via regioselective directed a-lithiation-alkylation and serendipitous base-promoted cyclization reaction, as key steps, has been developed. Directed a-lithiation of furan/thiophene-3-carboxaldehydes in their masked form and subsequent reaction with aldehydes efficiently provided in one-step, access to 3-formyl-2-furyl/thiophenylcarbinols, which are otherwise only accessible with difficulty. The 3-formyl-2-furylcarbinols are further elaborated to the synthesis of furo[2,3-d]tropones (also known as cyclohepta[b]furan-6-ones or furotropones) in good yields via sequential bismuth(III)chloride-catalyzed furfurylation and a novel base promoted cyclization reaction. This paper describes the general approach to the synthesis of 3-formyl-2-furylcarbinols and furotropones which could find potential applications in the synthesis of several bioactive natural products and pharmaceutics.
Page(s): 1103-1112
ISSN: 0975-0975(Online); 0376-4710(Print)
Appears in Collections:IJC-A Vol.52A(08-09) [August-September 2013]

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