A general approach to medium-sized ring ethers via hydrolytic and oxidative kinetic resolutions: stereoselective syntheses of (-)-cis-lauthisan and ( )-isolaurepan

作者：Tripathi Divya; Pandey Satyendra Kumar; Kumar Pradeep

来源：Tetrahedron, 2009, 65(11): 2226-2231.

DOI：10.1016/j.tet.2009.01.062

• Jacobson's Hydrolytic Kinetic Resolution (HKR)
• Oxidative resolution of secondary alcohol
• cis-Reductive cyclization
• Ring ether
• Oxepanes

A short and enantioselective approach to medium ring ethers and its application to the syntheses of (-)-cis-lauthisan and ( )-isolaurepan are described. The synthetic strategy features Jacobson's Hydrolytic Kinetic Resolution (HKR), oxidative resolution of secondary alcohol, and highly diastereoselective Et(3)SiH/TMSOTf-promoted reductive cyclization of a hydroxy ketone to give exclusively the different medium-sized cis-disubstituted cyclic ethers.

• 出版日期2009-3-14