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

Journal of the American Chemical Society
Barry M Trost, Hadi Gholami

Abstract

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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Citations

Aug 28, 2019·Angewandte Chemie·Barry M TrostGuillaume Mata
May 15, 2021·Organic Letters·Xinying CaiPeizhong Xie
May 3, 2019·Organic Letters·Catherine P McGeoughTimothy F Jamison

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