Total synthesis and stereochemical assignment of the spiroisoxazoline natural product (+)-calafianin.
Synthesis of the spiroisoxazoline natural product (+)-calafianin is reported using asymmetric nucleophilic epoxidation and nitrile oxide cycloaddition as key steps. Synthesis and spectral analysis of all calafianin stereoisomers led to unambiguous assignment of relative and absolute stereochemistry.
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Sujata
S
Bardhan
Daniel C
DC
Schmitt
John A
JA
Porco
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002942:Circular Dichroism; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D001688:Biological Products; D013141:Spiro Compounds; C412924:calafianin; D014443:Tyrosine