A general highly efficient access to prenylated phenolic natural products. Synthesis of colletochlorins B and D

✍ Scribed by Hiroyuki Saimoto; Tamejiro Hiyama

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 242 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)84050-2

✦ Synopsis

A general approach is reported for the synthesis of phenolic natural products having terpenoid side chains: (1) construction of the reouisite bromophenol ethers, (2) coupling the aromatic ring with a terpenoid chain through copper(I) ate complex, and (3) ether cleavage under neutral or basic conditions, and the feasibility of this strategy is demonstrated by efficient synthesis of colletochlorins B and D.

A group of natural products called "phenolic compounds" is characterized by multi-substituted (poly)hydroxylarenes which often involve a terpenoid side chain. ' Particular examples are antibiotics ascofuranone, 2 ascochlorin, 3 and colletochlorins , 4 all of which possess a fully substituted resorcinol moiety in common and exhibit a variety of biological activity.