Diels–Alder reactions of an elusive 1, 3-butadiene bearing 2-carboxy and 4-alkoxy substituents. Issue 38 (21st September 2016)

• Record Type: Journal Article
• Authors: Chen, Szu-Han; Chang, Che-Hsuan; Fang, Jim-Min
• Is Part Of: Tetrahedron letters. Volume 57:Issue 38(2016)
• Page Start: 4293
• Page End: 4296
• Publication Date: 2016-09-21
• Subjects: Diels–Alder reaction -- Influenza -- Oseltamivir -- Butadiene -- Dienophile; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.08.030
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An elusive 1, 3-butadiene having 2-carboxy and 4-alkoxy substituents is prepared. This reactive diene is trapped with dienophiles to give cycloaddition products. The cycloadduct from fumarate ester can be elaborated to oseltamivir (Tamiflu). Abstract: A reactive diene, ethyl 2-methylene-4-(pent-3-oxy)but-2-enoate, bearing electron-withdrawing carboxy and electron-donating pentoxy substituents is prepared and trapped in situ by a variety of dienophiles to form [4+2] cycloaddition products. Diels–Alder reaction of this diene with fumarate esters gives multiply substituted cyclohexenes that are useful for building the scaffold of oseltamivir.