• Bulletin of the Korean Chemical Society
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• v.23 no.1
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• pp.143-144
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• 2002

• Archives of Pharmacal Research
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• v.17 no.2
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• pp.104-108
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• 1994

trans-Ethyl 1, 2, 3, 4a, 5, 6, 8a-cotahydro-2-benzyl-4-hydroxy-6-methyl-5-isoquinoline-carboxylate was prepared by intramolecular Diels-Alder reaction as a precusor of newly designed aza-analogue of mevinolin.

• Journal of the Korean Chemical Society
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• v.38 no.9
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• pp.676-681
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• 1994

Diels-Alder adducts, carbacephems were obtained when 4-acetoxyazetidine-2-one or (3R,4R)-4-acetoxy-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one was reacted with 2-(tert-butyldimethylsilyloxy)-1,3-butadiene or with 3-(tert-butyldimethylsilyloxy)-1,3-pentadiene. When tert-butyldiemethylsilyl acrylate was used as the diene, products in which was acetoxy group of 4-acetoxyazetidin-2-one derivatives was substituted by an acryloyloxy group were isolated. When the same reaction was carried out with 4-phenylsulfonylazetidin-2-one as a dienophile with 2-(tert-butyldimethylsilyloxy)-1,3-butadiene, 4-phenylsulfoyl-2-butanone was obtained instead of the expected carbacephem. When dimeric form of thiochalcone was reacted with 4-acetoxyazetidin-2-one in the presence of zinc chloride, the $\beta-lactam$ ring of the azetidin-2-one was destructed and no product was isolated. Also, the reaction of 2-trimethylsilyloxy-1-aza-1,3-butadiene, which was obtained from N-methylacrylamide by treatment of trimethylsilyl trifluoromethanesulfonate in the presence of triethylamine, with 4-acetoxyazetidin-2-one did not give any products.