Issue 17, 2020

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
23 Apr 2020
Accepted
26 May 2020
First published
26 May 2020

Org. Chem. Front., 2020,7, 2385-2390

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, 7, 2385 DOI: 10.1039/D0QO00484G

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