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0/9/15 26 C O 2 E t C O 2 E t C O 2 E t+2020/9/15 27 Birch還原 O RL i , l i q . N H3 E t O HO RC O2RC O2RN a , l i q . N H3E t O HL i , l i q . N H3 E t O H2020/9/15 28 4. Disconnection on Bifunctional groups ( 1) ?, ?unsaturated pounds ORR 1 R 2RO+OR 1 R 2A l d o lc o n d e s a t i o nO OO2020/9/15 29 O RL i , l i q . N H 3 E t O HO ROH C lM e O HOM e O M e OL i , l i q . N H 3 E t O HH C lM e O H2020/9/15 30 A rC O 2 H A r C H O + ( C H 3 C O ) 2 OP e r k i nR e a c t i o nO C H OA c 2 O , A c O N a 1 5 0 o C O C H C H C O 2 H( 2) ?, ?unsaturated carboxylic acid 2020/9/15 31 ( 3) ?Hydroxyester R C O 2 E tOO H RO HR 39。1 . N a O H , H 2 O2 . H 3 O + C O 2C H 3 C C HO RR 39。 C ( C O 2 E t ) 21 . O H2 . H 3 O+, R R 39。2020/9/15 1 Introduction to Organic Synthesis 有機(jī)合成初步 2020/9/15 2 合成化學(xué)家在舊的自然界旁又建起了一個新的自然界 R. B. Woodward E. J. Corey Retrosynthetic analysis 逆合成分析 The Noble Prize in 1990 20世紀(jì) 《 The Logic of Chemical Synthesis》 2020/9/15 3 1. Retrosynthetic analysis (逆合成分析 ) In this procedure the target molecule is transformed progressively into simpler structures by disconnecting selected carboncarbon bonds. These disconnections rest on transforms, which are the reverse of plausible synthetic constructions. Each simpler structure, so generated, bees the starting point for further disconnections, leading to a branched set of interrelated intermediates. A retrosynthetic transform is depicted by the = symbol, as shown in next s