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Syntheses of (+)‐ and (–)‐Methyl 8‐Epinonactate and (+)‐ and (–)‐Methyl Nonactate
Author(s) -
Warm Aleksander,
Vogel Pierre
Publication year - 1987
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19870700319
Subject(s) - chemistry , mitsunobu reaction , alkyl , resolution (logic) , displacement (psychology) , chromatography , medicinal chemistry , organic chemistry , stereochemistry , psychology , artificial intelligence , computer science , psychotherapist
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.