Synthesis of (+)-Greek Tobacco Lactone via a Diastereoablative Epoxidation and a Selenium-Catalyzed Oxidative Cyclization

An asymmetric synthesis
of the C11-homoterpenoid (+)-Greek
tobacco lactone is developed starting from readily available (R)-linalool. The synthesis is comprised of four operations
and features a diastereoablative epoxidation and an oxidative tetrahydropyran
formation using vanadium-, palladium-, and selenium-catalyzed cyclizations.

本研究开发了一条以易于获取的(R)-芳樟醇（(R)-linalool）为起始原料，不对称合成C11高萜类化合物（C11-homoterpenoid）(+)-希腊烟草内酯（(+)-Greek tobacco lactone）的路线。该合成路线仅包含四步操作，其核心特色为非对映异构消融型环氧化反应，以及通过钒、钯、硒催化的环化反应实现的氧化型四氢吡喃环生成过程。