Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 6, Pages 2495-2500Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c13370
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Funding
- National Natural Science Foundation of China [22125109, 21871230]
- Zhejiang Provincial Natural Science Foundation of China [LZ22B020002]
- National Ten Thousand Talent Program [W03070091]
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A new method has been developed for the efficient assembly of diversely functionalized polyquinane frameworks, leading to asymmetric total syntheses of various tetraquinane natural products in a concise and divergent manner.
A hydrogen atom transfer (HAT)-initiated Dowd-Beckwith rearrangement reaction was developed, which enables the efficient assembly of diversely functionalized polyquinane frameworks. By incorporation of an iridium-catalyzed regio- and enantioselective hydrogenation and a diastereocontrolled ODI-[5+2] cycloaddition/pinacol rearrangement cascade reaction, the asymmetric total syntheses of eight tetraquinane natural products, including (-)-crinipellins A-F and (-)-dihydrocrinipellins A and B, have been achieved in a concise and divergent manner.
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