SYNTHESIS OF (+)- AND (-)-METHYL 8-EPINONACTATE AND (+)- AND (-)-METHYL NONACTATE

Article abstract of DOI:10.1002/hlca.19870700319

n 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 (-)-maethyl nonactate ((+)- and (-)-3) were obtained from (+)- and (-)-4, respectively, by Mitsunobu displacement reactions.Optical resolution of (+/-)-9 via cromatographic separation of the corresponding N-methyl-S-alkyl-S-phenylsulfoximides 24 and 25 yielded the starting material (+)- and (-)-9, respectively.