From Stereodefined Cyclobutenes to Dienes: Total Syntheses of Ieodomycin D and the Southern Fragment of Macrolactin A

Organic Letters
Caroline SourisNuno Maulide

Abstract

A copper-promoted flexible synthesis of cyclobutenes carrying simple alkyl chains, enabling even the most hindered nucleophiles to be employed, has been developed. The versatility of this approach was exemplified by a short total synthesis of ieodomycin D and a straightforward preparation of the southeastern fragment of macrolactin A. The latter features a late-stage, double cyclobutene electrocyclic ring opening that directly delivers a bis-diene of defined geometry.

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Citations

Jan 14, 2017·The Journal of Organic Chemistry·Bernd Schmidt, Stephan Audörsch
May 28, 2016·Chemistry : a European Journal·Benito AlcaideCarlos Lázaro-Milla
Jul 13, 2017·Journal of the American Chemical Society·M Elena de OrbeAntonio M Echavarren
Apr 10, 2018·Chemical Science·Bryce N ThomasRylan J Lundgren
Jul 14, 2018·Angewandte Chemie·Job Boekhoven, Dorian Didier
Dec 6, 2019·Mini Reviews in Medicinal Chemistry·Aurelio Ortiz, Estibaliz Sansinenea

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