Syntheses of (+)‐ and (–)‐Methyl 8‐Epinonactate and (+)‐ and (–)‐Methyl Nonactate

Abstract

Abstract In four synthetic steps, (+)‐ and (–)‐methyl 8‐epinonactate ((+)‐ and (–)− 4 ) have been derived from (+)‐ and (–)‐7‐oxabicyclo[2.2.1]heptan‐2‐one ((+)‐ and (–)− 9 ), respectively. The (+)‐ and (–)‐methyl nonactate ((+)‐ and (–)− 3 ) were obtained from (+)‐ and (–)− 4 , respectively, by Mitsunobu displacement reactions. Optical resolution of (±)− 9 via chromatographic separation of the corresponding N ‐methyl‐ S ‐alkyl‐ S ‐phenylsulfoximides 24 and 25 yielded the starting materials (+)‐ and (–)− 9 , respectively.