Issue 14, 2019

Asymmetric total synthesis of cryptoconcatone I

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.

Graphical abstract: Asymmetric total synthesis of cryptoconcatone I

Supplementary files

Article information

Article type
Paper
Submitted
18 Feb 2019
Accepted
11 Mar 2019
First published
12 Mar 2019

Org. Biomol. Chem., 2019,17, 3552-3566

Asymmetric total synthesis of cryptoconcatone I

R. K. Acharyya, P. Pal, S. Chatterjee and S. Nanda, Org. Biomol. Chem., 2019, 17, 3552 DOI: 10.1039/C9OB00399A

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