Stereocontrolled assembly of tetrasubstituted tetrahydrofurans: a concise synthesis of virgatusin.
The condensation of substituted allylsiloxanes with aldehydes leads to the highly stereoselective construction of 2,3,4,5-tetrasubstituted tetrahydrofurans. With electron-rich aryl and alpha,beta-unsaturated aldehydes as substrates, the stereochemical outcome at C5 can be dictated by appropriate choice of Lewis acid. The reaction has been applied to a concise (nine step) synthesis of (+)-virgatusin (ent-1). [reaction: see text]
Akindele
Tito
T
School of Chemistry, University of Leeds, Leeds LS2 9JT, U.K.
Marsden
Stephen P
SP
Cumming
John G
JG
D000447:Aldehydes / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000737:chemistry*; D015394:Molecular Structure; D012833:Siloxanes / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D005663:Furans; D017705:Lignans; D012833:Siloxanes; C511226:virgatusin