Asymmetric total synthesis of batzelladine D.
[formula: see text] The first enantioselective total synthesis of a batzelladine alkaloid is described. The central reaction in the synthesis of (-)-batzelladine D (2) is a tethered Biginelli condensation of a guanidine aldehyde and an acetoacetic ester to generate a 7-substituted-1-iminohexahydropyrrolo-[1,2-c]pyrimidine intermediate having the anti stereochemistry of the methine hydrogens flanking the pyrrolidine nitrogen.
Cohen
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F
Department of Chemistry, University of California, Irvine 92697-2025, USA.
Overman
L E
LE
Sakata
S K
SK
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D011161:Porifera / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D011743:Pyrimidines; C410707:batzelladine D