Synthetic study of Vertihemiptellide A : an antimycobacterial agent

2011 Fiscal Year Final Research Report

• Project/Area Number: 22890170
• Research Category: Grant-in-Aid for Research Activity Start-up
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Tohoku Pharmaceutical University
• Principal Investigator: NARITA Koichi 東北薬科大学, 薬学部, 助手 (20584460)
• Project Period (FY): 2010 – 2011
• Keywords: ベルチヘミプテリドA / 抗結核薬 / 二量化反応 / 全合成

Research Abstract

Vertihemiptellide A, a unique diketopiperazine dimer with antimycobacterial activity, was isolated from the insect pathogenic fungus Verticillium hemipterigenum BCC 1449 by Isaka and co-workers. The monomeric epidithiodiketopiperazine equivalent of vertihemiptellide A was synthesized from glycine derivative.α-Sulfenylation of diketopiperazine was achieved by nucleophilic addition of PMB-SH to acyliminium ion generated in situ fromα-hydroxylated diketopiperazine under acidic condition.