BIOMIMETIC CYCLIZATION OF HEDYCARYOL DERIVATIVES. UNEXPECTED CYCLIZATION OF PHENYL SULFIDES WITH METHYL IODIDE

Article abstract of DOI:10.1016/S0040-4039(01)90367-3

Four isomeric hedycaryol phenyl sulfides, when reacted with MeI, yielded eudesmol derivatives with different stereochemistry from that of the acid cyclization products of the corresponding hedycaryols.New stereoisomers of α- and β-eudesmols, β-dehydroparadisiol and a defensive substance of termite were synthesized.Nephthenol phenyl sulfide yielded a 14-membered tetraene.