Synthesis

Total synthesis of the leucetta-derived alkaloid calcaridine A

PB Koswatta, R Sivappa, HVR Dias, CJ Lovely

Index: Koswatta, Panduka B.; Sivappa, Rasapalli; Dias, H. V. Rasika; Lovely, Carl J. Synthesis, 2009 , # 17 p. 2970 - 2982

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Citation Number: 9

Abstract

Abstract A biomimetically guided total synthesis of the Leucetta-derived aminoimidazole alkaloid, calcaridine A, is described. The synthesis relies on position selective metalations of a 4, 5-diiodoimidazole derivative to provide a tetrasubstituted imidazole. Subjection of this polysubstituted imidazole derivative to oxidative rearrangement with a Davis oxaziridine provides the corresponding imidazolone core of calcaridine A.