Intramolecular Prins cyclisations for the stereoselective synthesis of bicyclic tetrahydropyrans.
Methyl (4E,7R)-7-hydroxyoctanoate was prepared in 71% yield from ethyl (R)-3-hydroxybutanoate and on reaction with a series of aldehydes in the presence of TMSOTf gave bicyclic oxygen heterocycles in good yields and with the creation of three new stereogenic centres in a single pot.
Elsworth
Jon D
JD
School of Chemistry, University of Bristol, Bristol, UK BS8 1TS.
Willis
Christine L
CL
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002210:Caprylates / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D002210:Caprylates; D011714:Pyrans; C529034:methyl (4E,7R)-7-hydroxyoctanoate