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Propene as an Atom-Economical Linchpin for Concise Total Synthesis of Polyenes: Piericidin A

Cite this: J. Am. Chem. Soc. 2018, 140, 37, 11623–11626
Publication Date (Web):September 1, 2018
https://doi.org/10.1021/jacs.8b08974
Copyright © 2018 American Chemical Society

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    Abstract

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    A concise and convergent total synthesis of piericidin A is disclosed. The synthesis hinges on the utilization of propene as a synthetic linchpin to merge the properly elaborated alkyne fragments, leading to the 1,3,6-triene motif of piericidin A. Utilization of propene as a unique alkene, capable of sequential coupling with two alkynes, is further illustrated in the context of various 1,3,6-triene products. The latter process proceeds with high atom economy and efficiently gives rise to complex frameworks from readily accessible alkyne substrates. This strategic C–C bond formation offers an orthogonal paradigm in the design of synthetic routes, leading to higher step economy and more efficient syntheses of polyunsaturated natural products.

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    • Experimental procedures, analytical data (1H NMR, 13C NMR, MS, IR, and [α]D) for all new compounds, additional reaction optimization tables (PDF)

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