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–TiCl4—nBu3N-mediated cascade annulation of ketones with α-ketoesters: a facile synthesis of highly substituted fused γ-alkylidene- butenolides

Abstract

A facile protocol for the synthesis of highly substituted fused γ-alkylidene butenolides using direct annulation of ketones with α-ketoesters, which proceeds through TiCl4-n-Bu3N mediated aldol addition followed by intramolecular enol-lactonization/cyclization cascade is reported. Diverse 6-5, 7-5 and 8-5 fused bicyclic γ-ylidene butenolides and highly substituted monocyclic analogs related to biologically relevant natural products were prepared from readily accessible ketone and α-ketoester building blocks. Highly step-economic cascade nature, good substrate scope, easy access to complex products in good to excellent yields, gram-scalability, demonstration of synthetic utility, unambiguous structural confirmation through X-ray crystallography analyses and analogy are salient features of this work.

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Publication details

The article was received on 20 Mar 2019, accepted on 16 May 2019 and first published on 17 May 2019


Article type: Paper
DOI: 10.1039/C9OB00649D
Org. Biomol. Chem., 2019, Accepted Manuscript

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    –TiCl4—nBu3N-mediated cascade annulation of ketones with α-ketoesters: a facile synthesis of highly substituted fused γ-alkylidene- butenolides

    M. N. Palange, R. G. Gonnade and R. Kontham, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB00649D

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