Enantiospecific, biosynthetically inspired formal total synthesis of (+)-liphagal.
A biosynthetically inspired synthesis of (+)-liphagal has been achieved from (+)-sclareolide in 13 steps (9% overall yield). The key step is a biomimetic ring expansion of a highly stabilized benzylic carbocation, which generates the seven-membered ring and the benzofuran of the natural product in a single cascade reaction.
George
Jonathan H
JH
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. jonathan.george@chem.ox.ac.uk
Baldwin
Jack E
JE
Adlington
Robert M
RM
D004224:Diterpenes / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D004224:Diterpenes; D013729:Terpenes; C513880:liphagal; C109395:sclareolide