Total Synthesis of Asperchalasines A, D, E, and H. Issue 43 (13th September 2018)

• Record Type: Journal Article
• Authors: Long, Xianwen; Ding, Yiming; Deng, Jun
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 43(2018)
• Page Start: 14221
• Page End: 14224
• Publication Date: 2018-09-13
• Subjects: biomimetic synthesis -- cycloaddition -- dimers -- natural products -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201808481
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The first total syntheses of the cytochalasan dimers asperchalasines A, D, E, and H have been accomplished. The key steps of the synthesis include a highly stereoselective intermolecular Diels–Alder reaction and a Horner–Wadsworth–Emmons macrocyclization to establish the key monomer aspochalasin B, and an intermolecular Diels–Alder reaction followed by a biomimetic oxidative heterodimerization by 5+2 cycloaddition to furnish asperchalasine A. The synthetic efforts provide insight into the biosynthetic pathway of cytochalasan dimers and enables the further study of their biological properties. Abstract : Making two into one : Total syntheses of asperchalasines A, D, E, and H are reported. The key steps of the synthesis include an intermolecular Diels–Alder (DA) reaction and a Horner–Wadsworth–Emmons macrocyclization to establish the key monomer aspochalasin B, and an intermolecular DA reaction followed by a biomimetic oxidative heterodimerization to furnish asperchalasine A. This synthesis provides insight into the biosynthetic pathway of cytochalasan dimers.