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Communication | Special issue | Vol 97, No. 2, 2018, pp.712-718
Published online, 29th March, 2018
DOI: 10.3987/COM-18-S(T)71
First Asymmetric Total Synthesis of (-)-Isostemonamine and Kinetic Analysis of Its Isomerizations

Takayuki Iwata, Taishi Tomiyama, Satoshi Fujita, and Mitsuru Shindo*

*Institute for Materials Chemistry and Engineering (IMCE), Kyushu University, 6-1, Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan

Abstract

The first asymmetric total synthesis of (−)-isostemonamine is reported herein. The key reactions include the regioselective oxidation of the diketone, which is reported to be an intermediate in our synthesis of (−)-stemonamine. The chiral high-performance liquid chromatography (HPLC) analysis of the racemization and epimerization of (−)-isostemonamine revealed that isostemonamine isomerizes significantly faster than stemonamine.