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Diastereoselective construction of the benzannulated spiroketal core of chaetoquadrins enabled by a regiodivergent cascade

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Abstract

A remarkable acid-mediated methodology for the regiodivergent construction of a biologically interesting tricyclic benzannulated spiroketal skeleton with diastereomeric specificity was uncovered using a variety of readily available phenol substrates. The approach mainly refers to an intriguing hemi-ketalization/dehydration/Michael addition/ketalization cascade process, offering a viable synthetic strategy to efficiently access analogs of chaetoquadrins.

Graphical abstract: Diastereoselective construction of the benzannulated spiroketal core of chaetoquadrins enabled by a regiodivergent cascade

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Article information


Submitted
23 Apr 2020
Accepted
26 May 2020
First published
26 May 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Diastereoselective construction of the benzannulated spiroketal core of chaetoquadrins enabled by a regiodivergent cascade

L. Shi, S. Wang, L. Huo, M. Gao, W. Zhang, X. Lu, S. Qiu, H. Liu and H. Tan, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00484G

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