TESOTf-induced rearrangement of quinols. Efficient construction of the fully functionalized carbon skeleton of the griseusins by a divergent-reconvergent approach.

Organic Letters
K A ParkerYung-hyo Koh

Abstract

[reaction: see text] The "reverse polarity" or "umpolung" strategy for the total synthesis of aryl C-glycosides was developed in the context of the antibiotic (-)-griseusin B. Although a key reaction in a model sequence for the total synthesis produced two structurally divergent products, both were converted to the same advanced model intermediate that contains the complete carbon skeleton and (except for the extraneous oxygen substituent in the model series) the functional group pattern of the griseusins.

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Citations

Oct 5, 2019·Chemical Science·Yinan ZhangJon S Thorson
Aug 1, 2015·Angewandte Chemie·Yinan ZhangJon S Thorson
Jun 14, 2013·The Journal of Organic Chemistry·Sarvesh KumarConrad Santini
Sep 16, 2017·Chemical Reviews·You Yang, Biao Yu
Dec 13, 2017·The Journal of Organic Chemistry·Soumen Chakraborty, Dipakranjan Mal

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