545363-19-7Relevant academic research and scientific papers
Stereocontrolled total synthesis of (-)-aspidophytine
Sumi, Shinjiro,Matsumoto, Koji,Tokuyama, Hidetoshi,Fukuyama, Tohru
, p. 8571 - 8587 (2007/10/03)
The enantioselective stereocontrolled total synthesis of aspidophytine is described. The key indole intermediate was prepared by radical cyclization of 2-alkenylphenylisocyanide, followed by Sonogashira-coupling with a highly functionalized terminal acetylene. The 11-membered cyclic amine, a precursor for the formation of the aspidosperma skeleton, was synthesized using nitrobenzenesulfonamide chemistry. After construction of the pentacyclic skeleton, the lactone ring was formed to complete the total synthesis.
Enantioselective total synthesis of aspidophytine
Sumi, Shinjiro,Matsumoto, Koji,Tokuyama, Hidetoshi,Fukuyama, Tohru
, p. 1891 - 1893 (2007/10/03)
(Matrix presented) An enantioselective total synthesis of aspidophytine is described. The indole fragment bearing a cis-alkene substituent was efficiently prepared through radical cyclization of a 2-alkenylphenylisocyanide followed by Sonogashira coupling of the generated 2-iodoindole derivative with a functionalized acetylene unit. After formation of the 11-membered cyclic amine, the aspidosperma skeleton and lactone ring were constructed to complete the total synthesis.
