Organic Letters
Organic Letters
5 years ago

Total Syntheses of Naucleamides A–C and E, Geissoschizine, Geissoschizol, (E)-Isositsirikine, and 16-epi-(E)-Isositsirikine

Total Syntheses of Naucleamides A–C and E, Geissoschizine, Geissoschizol, (E)-Isositsirikine, and 16-epi-(E)-Isositsirikine
Paruke Aibibula, Lei Li, Qianlan Jia, Yanxing Jia
A divergent approach for the enantioselective total synthesis of eight monoterpenoid indole alkaloids was developed. The approach allows the first total syntheses of naucleamides A–C and E in only 6–8 steps and also enables the efficient synthesis of geissoschizine, geissoschizol, (E)-isositsirikine, and 16-epi-(E)-isositsirikine in 10–11 steps from commercially available crotonic aldehyde. The synthesis features a one-pot organocatalyzed asymmetric Michael addition/Pictet–Spengler reaction. Notably, biomimetic synthesis of naucleamide E was achieved by oxidative cyclization of naucleamide A.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00983

DOI: 10.1021/acs.orglett.7b00983

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