Synthetic study of Vertihemiptellide A : an antimycobacterial agent

• 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
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥3,042,000 (Direct Cost: ¥2,340,000、Indirect Cost: ¥702,000); Fiscal Year 2011: ¥1,404,000 (Direct Cost: ¥1,080,000、Indirect Cost: ¥324,000); Fiscal Year 2010: ¥1,638,000 (Direct Cost: ¥1,260,000、Indirect Cost: ¥378,000)
• 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.