Total synthesis of (+/-)-calcaridine A and (+/-)-epi-calcaridine A.
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.
Koswatta
Panduka B
PB
Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, USA.
Sivappa
Rasapalli
R
Dias
H V Rasika
HV
Lovely
Carl J
CJ
D000470:Alkaloids / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D007093:Imidazoles; D009930:Organic Chemicals; C533356:calcaridine A