An approach to seco-prezizaane sesquiterpenoids: enantioselective total synthesis of (+)-1S-minwanenone.
A strategy of general applicability toward seco-prezizaane sesquiterpenes, from a chiral, tricyclic synthon, readily available via an enzymatic resolution step from the Diels-Alder adduct of cyclopentadiene and p-benzoquinone, has been devised. Our approach enables harnessing of the stereochemical proclivities of the norbornyl system to install the desired stereochemistry at the key stereogenic centers. Recourse to an interesting stratagem to realign a stereochemical divergence into stereoreconvergence forms the cornerstone of our successful approach. The first total synthesis of (+)-1S-minwanenone, a prototypical member of seco-prezizaane subclass, has been accomplished.
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. gm@orgchem.iisc.ernet.in
Goverdhan
G
Mehta
Harish M
HM
Shinde
D000447:Aldehydes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
C579732:1S-minwanenone; D000447:Aldehydes; D001643:Bridged Bicyclo Compounds; D012717:Sesquiterpenes