A method of preparing a saturated monocyclic hydrocarbon compound and an intermediate therefor

摘要

Disclosed is a method of preparing a saturated monocyclic hydrocarbon compound having high optical purity and an intermediate therefor from an easily available starting material. A vinyl group is introduced to compound (6), which is synthesized from levoglucosenone to obtain compound (7). The double bond of the vinyl group of compound (7) is oxidatively cleaved and a hydroxyl group is protected to obtain compound (9). The obtained compound (9) was intramolecularly alkylated by treating with a base to give compound (10). Then, compound (10) is reduced to give compound (11). The primary hydroxyl group is selectively esterified to obtain the desired saturated monocyclic hydrocarbon compound (1). where R<1>, R<2>, and R<3> are an alkyl group and an X<2> group is a leaving group which is possible to remove as OX<2>.