Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling

Hengtao Wang; Xiunan Zhang; Pingping Tang

doi:10.1039/C7SC03293E

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Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling†

Hengtao Wang,^a Xiunan Zhang^a and Pingping Tang

*^ab

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* Corresponding authors

^a State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
E-mail: ptang@nankai.edu.cn

^b Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China

Abstract

The first total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A have been accomplished using a nickel-catalyzed cross coupling of alkyl bromide with vinyl stannane as the final step. The other key steps include late-stage C(sp³)–H bromination, the oxidative cleavage of a diol to provide the requisite ketone and ester for schilancidilactones A and B, and Dieckmann-type condensation to generate the A ring of schilancitrilactone A and 20-epi-schilancitrilactone A.

This article is part of the themed collections: Celebrating 100 Years of Chemistry at Nankai University and In celebration of Chinese New Year

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DOI: https://doi.org/10.1039/C7SC03293E
Article type: Edge Article
Submitted: 28 7 2017
Accepted: 29 8 2017
First published: 30 8 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2017,8, 7246-7250

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Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling

H. Wang, X. Zhang and P. Tang, Chem. Sci., 2017, 8, 7246 DOI: 10.1039/C7SC03293E

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Chemical Science

Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling†

Abstract

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Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling

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