Issue 10, 2017
From the journal:

Chemical Science

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 Zhanga  and  Pingping Tang ORCID logo *ab  

* 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.

Graphical abstract: 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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Article information

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

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

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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