Issue 10, 2017

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
28 7月 2017
Accepted
29 8月 2017
First published
30 8月 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

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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