Total Syntheses of Asperchalasines A–E

• DOI: 10.1002/ange.201808249
• Publication Date: 2018-09-07T08:33:48Z
• Authors: Ruiyang Bao; Chong Tian; Haoyu Zhang; Zhiguo Wang; Zhen Dong; Yuanhe Li; Mohan Gao; Haolin Zhang; Gang Liu; Yefeng Tang
• Keywords: Diels–Alder reaction; Ring-Closing Metathesis; Salt metathesis reaction

Abstract The first total syntheses of asperchalasines A–E, a collection unprecedented merocytochalasans, are reported. Aspochalasin B, key tricyclic cytochalasan monomer, was synthesized through unified approach that hinges on Diels–Alder reaction and ring‐closing metathesis reaction. bioinspired reactions aspochalasin B with different epicoccine precursors were then explored, which enabled the divergent access heterodimers B–E as well related congeners. Furthermore, heterotrimer asperchalasine A obtained from one unit two units biomimetic followed by an oxidative [5+2]‐cycloaddition.