Bi(OTf)3-promoted cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters for the construction of polycyclic bridged pyrano-furopyranones

Akshay B. Rathod; Balasaheb R. Borade; Pooja I. Sambherao; Ravindar Kontham

doi:10.1039/D3OB01862H

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Bi(OTf)₃-promoted cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters for the construction of polycyclic bridged pyrano-furopyranones†

Akshay B. Rathod,^ab Balasaheb R. Borade,^ab Pooja I. Sambherao^ab and Ravindar Kontham

*^ab

Author affiliations

* Corresponding authors

^a Organic Chemistry Division, CSIR-National Chemical Laboratory Dr Homi Bhabha Road, Pune-411008, India
E-mail: k.ravindar@ncl.res.in

^b Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India

Abstract

An efficient protocol for constructing complex three dimensional polycyclic bridged chromano-furopyranones and pyrano-furopyranones (closely related to bioactive natural products) via bismuth(III)-catalyzed cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters is presented. This process involves intermolecular Michael addition, intramolecular hemiketalization, lactonization, formation of one C–C bond and two C–O bonds, rings, and contiguous stereocenters.

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Article information

DOI: https://doi.org/10.1039/D3OB01862H
Article type: Communication
Submitted: 16 Nov 2023
Accepted: 20 Dec 2023
First published: 20 Dec 2023

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Org. Biomol. Chem., 2024,22, 496-500

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Bi(OTf)₃-promoted cascade annulation of hydroxy-pyranones and unsaturated γ-ketoesters for the construction of polycyclic bridged pyrano-furopyranones

A. B. Rathod, B. R. Borade, P. I. Sambherao and R. Kontham, Org. Biomol. Chem., 2024, 22, 496 DOI: 10.1039/D3OB01862H

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Organic & Biomolecular Chemistry