Abstract
AbstractIn an attempted synthesis of oseltamivir, D‐serine was used to prepare (R)‐Garner aldehyde, which reacted with vinylzinc reagent to give an alcohol product predominating in the (1′R,4S)‐isomer. After the alcohol was protected as p‐methoxybenzyl ether, the N,O‐acetal was hydrolyzed and oxidized to an aldehyde, which underwent Reformatsky‐type reaction with ethyl α‐(bromomethyl)acrylate by promotion of indium to give an addition product readily for ring‐closure metathesis to afford 3‐alkoxy‐4‐amido‐5‐hydroxy‐1‐cyclohexenecarboxylates. After activation of the 5‐hydroxy group as methanesulfonate, an attempted substitution reaction with sodium azide gave unexpectedly a cyclic carbamate via an intramolecular nucleophilic attack of the 4‐tert‐butoxycarbamate group.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
