A new route to (±)- erythro-roccellic acid and chaetomellic anhydride C through functional rearrangement, promoted by n-propylamine or CH 3ONa/CH 3OH, of N-propyl-3-chloro-4-dichloromethyl-3-dodecylpyrrolidin-2-one

Laurent De Buyck,Chiara Danieli,Franco Ghelfi,Ugo M Pagnoni,Andrew F Parsons,Mariella Pattarozzi,Fabrizio Roncaglia

doi:10.1016/j.tet.2005.01.086

A new route to (±)- erythro-roccellic acid and chaetomellic anhydride C through functional rearrangement, promoted by n-propylamine or CH 3ONa/CH 3OH, of N-propyl-3-chloro-4-dichloromethyl-3-dodecylpyrrolidin-2-one

Laurent De Buyck, Chiara Danieli + Show 5 more

https://doi.org/10.1016/j.tet.2005.01.086

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Journal: Tetrahedron	Publication Date: Feb 11, 2005
Citations: 17

Affiliation: University of York

#Catalyzed Atom Transfer Radical Cyclization #Chaetomellic Anhydride + Show 7 more

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Abstract

The rearrangement of a trichloro-pyrrolidin-2-one, prepared by the CuCl–TMEDA catalyzed atom transfer radical cyclization of N-alkyl- N-(3-chloro-2-propenyl)-2,2-dichloromyristamide, with n-propylamine or CH 3ONa/CH 3OH, is the key step of a new, short and inexpensive route to chaetomellic anhydride C and (±)- erythro-roccellic acid.

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