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Total Synthesis of (±)-Calcaridine A and (±)-epi-Calcaridine A

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posted on 06.11.2008, 00:00 authored by Panduka B. Koswatta, Rasapalli Sivappa, H. V. Rasika Dias, Carl J. Lovely
The first total synthesis of the Leucetta alkaloid calcaridine A is described based on a biosynthetic postulate. Application of an oxidative rearrangement of a 4,5-disubstituted imidazole leads to the formation of both calcaridine A and epi-calcaridine A. An X-ray crystal structure determination on the latter has allowed the assignment of the relative configuration of the epimeric natural product and calcaridine A by extrapolation.