Total synthesis of the sphingolipid biosynthesis inhibitor fumonisin B(1).
The first total synthesis of the sphingolipid biosynthesis inhibitor fumonisin B(1) has been achieved. This convergent synthesis utilizes oxonia Cope rearrangements to prepare two key homoallylic alcohols, which are then functionalized to the primary components A and B for cross-coupling. Other highlights of our approach include a new and efficient synthesis of the diprotected tricarballylic acid C and a global deprotection strategy as the final step.
Pereira
Claney L
CL
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Chen
Yi-Hung
YH
McDonald
Frank E
FE
D037341:Fumonisins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008968:Molecular Conformation; D013107:Sphingolipids / Q000096:biosynthesis*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D037341:Fumonisins; D013107:Sphingolipids; C056933:fumonisin B1