Total synthesis and absolute stereochemistry of integric acid.
An efficient total synthesis of integric acid is described starting from the Wieland-Miescher ketone. Key steps involve a one-step orthogonal deprotection/protection strategy of a thioacetal/aldehyde and the selective oxidative cleavage of a prenyl group in the presence of two other unsaturated moieties. The synthesis of both C4' diastereoisomers of integric acid delivered unambiguous evidence for (S)-stereochemistry at the C4' position.
Waalboer
Dennis C J
DC
Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, NL-6525 AJ Nijmegen, The Netherlands.
van Kalkeren
Henri A
HA
Schaapman
Mark C
MC
van Delft
Floris L
FL
Rutjes
Floris P J T
FP
D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002264:Carboxylic Acids; D009281:Naphthalenes; C120097:integric acid