Abstract
AbstractUnder Mannich reaction conditions (diethylamine and formaldehyde in toluene under reflux) lasalocid (1) undergoes a unique transformation in which the carboxyl group is replaced by a diethylaminomethyl group. The resulting Mannich base 2 was converted back to lasalocid, proving that none of the other chemical and stereochemical features of the molecule were disturbed. Like other phenolic Mannich bases, the one derived from lasalocid readily alkylated mercaptans.The known thermal and base‐induced retro‐aldol degradations of lasalocid both produce a ketone fragment 9 containing the cyclic ether units. Baeyer‐Villiger oxidation of this ketone afforded a carboxylic acid fragment which still contained these ether units. The normal regiochemistry involved in oxidizing this ketone (RCH2COCHR′R″ type) was cleanly reversed by first converting it into the hydroxymethylidene derivative 10.
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.
