| 摘要 |
A 4-alkenyl-2-azetidinone derivative is provided to have a novel structure of introducing 1,3-diene-2-yl or 1,2,4,5-hexatetraene-3-yl into a C-4 position of beta-lactam, thereby being usefully used as a diene reaction material for a Diels-Alder reaction. A 4-alkenyl-2-azetidinone derivative is represented by a formula(1), wherein Q is CH or C=CH; R^1 is H, or C1-6 hydroxyalkyl or protected hydroxyalkyl; and R^2 is H, C1-6 alkyl, or phenyl. A method for preparing the derivative of the formula(1) comprises the steps of: (a) reacting a propargyl halide derivative represented by a formula(2) with indium to prepare an organic indium reagent represented by a formula(3); and (b) reacting the reagent of the formula(3) with 4-acetoxy-2-azetidinone represented by a formula(4) to prepare the derivative of the formula(1), wherein X is halogen; Y is -C- or -C-C=C-; n is 0 or 2; and Q, R^1, and R^2 are same as defined above. A method for preparing a multicyclic compound represented by a formula(6a) or (6b) comprises a step of subjecting the compound of the formula(1) and a dienophile represented by a formula(5a) or (5b) to Diels-Alder reaction, wherein Q, R^1, and R^2 are same as defined above; and each E^1, E^2, E^3, E^4, E^5, and E^6 is H, cyano, C(O)R, C(O)OR, or C(O)NR2(wherein R is H or C1-6 alkyl).
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