Total Synthesis of Proposed Structure of Yuremamine and All Diastereomers Using [3+2]-Cycloaddition of Platinum-Containing Azomethine Ylide

• Published in: Chemistry, an Asian journal Vol. 10; no. 9; pp. 1850 - 1853
• Main Authors: Ohyama, Tomoya, Uchida, Masako, Kusama, Hiroyuki, Iwasawa, Nobuharu
• Format: Journal Article
• Language: English
• Published: Germany Blackwell Publishing Ltd 01.09.2015; Wiley Subscription Services, Inc
• Subjects: [3+2] cycloaddition; Azo Compounds - chemistry; azomethine ylide; Biological Products - chemical synthesis; Biological Products - chemistry; Chemistry; Cycloaddition Reaction - methods; Indoles - chemical synthesis; Indoles - chemistry; Mimosa - chemistry; Plant Extracts - chemical synthesis; Plant Extracts - chemistry; platinum; Platinum - chemistry; Stereoisomerism; Thiosemicarbazones - chemistry; total synthesis; yuremamine; platinum; azomethine ylide; total synthesis; yuremamine; [3+2] cycloaddition
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.201500491

Total synthesis of the proposed structure of yuremamine has been achieved for the first time based on the intermolecular [3+2]‐cycloaddition reaction of the platinum‐containing azomethine ylide. All the possible diastereomers of yuremamine were also synthesized via the common intermediate. Through these syntheses, it was confirmed that the proposed structure of yuremamine and the diastereomers differ from the natural product. The total synthesis of the proposed structure of yuremamine and its diastereomers has been achieved based on the [3+2]‐cycloaddition reaction of the platinum‐containing azomethine ylide. Its basic core skeleton, pyrrolo[1,2‐a]indole skeleton, was efficiently constructed by this method at an early stage of the synthesis and a straightforward, short‐step synthesis of the target products has been achieved.