☆ 4.8 Article

Rh(I)-Catalyzed [(3+2)+1] Cycloaddition of 1-Yne/Ene-vinylcyclopropanes and CO: Homologous Pauson-Khand Reaction and Total Synthesis of (±)-α-Agarofuran

ORGANIC LETTERS (2010)

期刊

ORGANIC LETTERS

卷 12, 期 11, 页码 2528-2531

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ol100625e

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Chemistry, Organic

资金

Natural Science Foundation of China [20825205, 20672005]
Ministry of Education of China [108001]
National Basic Research Program of China-973 Program [2010CB833203]

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摘要

A novel Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition, which can be regarded as a homologous Pauson-Khand reaction, was developed to synthesize bicyclic cyclohexenones and cyclohexanones, enabling a new approach for synthesis of six-membered carbocycles ubiquitously found in natural products and pharmaceutics. The significance of the Rh-catalyzed [(3 + 2) + 1] cycloaddition has been demonstrated by the total synthesis of a furanoid sesquiterpene natural product, a-agarofuran, in which the bicyclic skeleton was constructed by the [(3 + 2) + 1] reaction of 1-yne-VCP and CO.

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