Total Synthesis of (-)-Conophylline

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Presentation transcript:

Total Synthesis of (-)-Conophylline By Daniela Sustac Han-Ya, Y.; Tokuyama, H.; Fukuyama, T. Angew. Chem. Int. Ed. 2011, 50, 4884.

Introduction Isolated in 1992 (Tabernaemontana divaricata) Potential use in type I diabetes and cancer therapy; Bis(indole) alkaloid, unique furan connectivity between the two fragments.

Retrosysnthesis

Synthesis of Fragment A

Fragment A - continued

Synthesis of Amine Fukuyama JACS 2002, 124, 2137.

Fragment A - continued

Fragment A – done!

Fragment B

Fragments coupling

Previous studies JOC 1982, 47, 803.

Last Steps