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Asymmetric total synthesis of cryptoconcatone I
Ranjan Kumar Acharyya1, Pratik Pal, Shrestha Chatterjee
1Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, 721302, India. snanda@chem.iitkgp.ac.in.
Abstract:
Asymmetric total synthesis of the naturally occurring cryptoconcatone I, which possesses a γ-Z-butenolide framework, is described here for the first time. Asymmetric propargylation, E-selective cross metathesis, and regioselective reductive epoxide ring opening were employed to access the enantiopure terminal alkyne. Late stage bimetallic cascade cyclization of the alkyne with (Z)-3-bromoacrylic acid afforded the natural product in an efficient way.
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