First total synthesis of prunustatin A

• Published in: Tetrahedron letters Vol. 55; no. 6; pp. 1175 - 1177
• Main Authors: Yamakoshi, Shuhei, Kawanishi, Eiji
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 05.02.2014; Elsevier
• Subjects: 15-Membered ring; Anhydrides; chemical reactions; chemical structure; Chemistry; Chemistry, Organic; GRP78; Inhibitors; Macrocyclization; organic compounds; Physical Sciences; Proteins; Prunustatin A; Reformatsky reaction; Science & Technology; Synthesis (chemistry); Tetrahedrons; GRP78; Prunustatin A; Reformatsky reaction; Macrocyclization; 15-Membered ring; CHAPERONE DOWN-REGULATOR; STREPTOMYCES-VIOLACEONIGER; LACTONIZATION; MIXED ANHYDRIDE; CATALYSTS

[Display omitted] In this study, we achieved the first total synthesis of natural prunustatin A (1), a novel inhibitor of glucose-regulated protein 78 (GRP78) expression. A key feature included a 15-membered ring macrocyclization, which was successfully accomplished by employing Shiina macrolactoniz...