Total synthesis of syringolin A.
A convergent, efficient synthesis of syringolin A has been accomplished in 13 steps from commercially available materials, Garner's aldehyde and L-valine. The unnatural 3,4-dehydrolysine fragment was prepared using successive Johnson-Claisen/Curtius rearrangement reactions. The macrolactamization and late-stage introduction of the side chain will provide convenient access to analogues of this promising proteasome inhibitor.
Dai
Chunhui
C
Department of Chemistry, Boston University, Boston, Massachusetts 02215, USA.
Stephenson
Corey R J
CR
D000447:Aldehydes / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D044224:Pseudomonas syringae / Q000737:chemistry; D013237:Stereoisomerism; D014633:Valine / Q000737:chemistry*
D000447:Aldehydes; D010456:Peptides, Cyclic; C407267:syringolin A; D014633:Valine