161659-96-7Relevant articles and documents
2-Substituted 2,3-dihydro-4H-1,3-benzoxazin-4-ones: Novel auxiliaries for stereoselective synthesis of 1-β-methylcarbapenems
Kondo,Seki,Kuroda,Yamanaka,Iwasaki
, p. 2877 - 2884 (1997)
The dihydrobenzoxazone 9e, which is easily prepared from salicylamide 11 and cyclohexanone, serves as an efficient auxiliary in the synthesis of the 1-β-methylcarbapenem key intermediate 10. The stereocontrolled Reformatsky-type reactions of the acetoxyazetidinone 2 with the carboximides 6 gave the intermediates 7 with high diastereoselectivities in high chemical yields. The auxiliary 9e also acts as a good leaving guoup in the TMSCl-promoted Dieckmann-type cyclization leading to a 1-β-methylcarbapenem skeleton. By using this auxiliary, 10 was synthesized in 58% overall yield and four steps from 2.
2-Substituted 2,3-dihydro-4H-1,3-benzoxazin-4-ones: A novel auxiliary for stereoselective synthesis of 1-β-methylcarbapenems
Kondo,Seki,Kuroda,Yamanaka,Iwasaki
, p. 1096 - 1097 (2007/10/02)
-
