Journal
SYNTHESIS-STUTTGART
Volume -, Issue 17, Pages 2970-2982Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1216929
Keywords
2-aminoimidazole; oxidative rearrangement; metal-halogen exchange; oxaziridine; imidazolone
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Funding
- Robert A. Welch Foundation [Y-1362, Y-1289]
- NIH [GM065503]
- NSF provided funding [CHE-9601771, CHE-0234811]
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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.
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