Consice total synthesis of Mangromicins utilizing cascade reactions and development of new medicine for tropical disease

2016 Fiscal Year Final Research Report

• Project/Area Number: 15K18836
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Kitasato University
• Principal Investigator: Yamada Takeshi 北里大学, 感染制御科学府, 特任助教 (00608367)
• Project Period (FY): 2015-04-01 – 2017-03-31
• Keywords: 全合成 / 抗トリパノソーマ / マングロマイシン / ディークマン反応 / βラクトン / カスケード反応 / アフリカ睡眠病 / 多置換テトラヒドロフラン

Outline of Final Research Achievements

An enantioselective total synthesis of (+)-Mangromicin A has been accomplished. Naturally occurring mangromicins are novel anti-trypanosomal compounds, which have been discovered by our group. The tetrahydrofuran ring of mangromicin A, possessing a tetra-substituted carbon center, was constructed by Mukaiyama-type vinylogous alkylation via a cyclic oxocarbenium intermediate derived from γ-hydroxy ketone, with ideal stereoselectivity, and the 4-hydoxy-dihydropyrone scaffold was generated via Dieckmann cyclization at a late stage of the total synthesis. The reliable asymmetric synthesis of (+)-mangromicin A has revealed the absolute configuration of the naturally occurring mangromicin A.

Free Research Field

天然物合成化学