(1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene as a surrogate for (1E,3E)-1,4- diacetoxy-1,3-butadiene: a highly efficient synthesis of (+/-)-shikimic acid
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(1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene as a surrogate for (1E,3E)-1,4- diacetoxy-1,3-butadiene: a highly efficient synthesis of (+/-)-shikimic acid
Koreeda, Masato; Teng, Kelly; Murata, Toshiki
Koreeda, Masato; Teng, Kelly; Murata, Toshiki
1990
Citation:Koreeda,, Masato, Teng, Kelly, Murata, Toshiki (1990)."(1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene as a surrogate for (1E,3E)-1,4- diacetoxy-1,3-butadiene: a highly efficient synthesis of (+/-)-shikimic acid." Tetrahedron Letters 31(42): 5997-6000. <http://hdl.handle.net/2027.42/28968>
Abstract: The 5-step synthesis of (+/-)-shikimic acid has been achieved in 55% overall yield from (1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene, starting with its Diels-Alder reaction with 2-(trimethylsilyl)ethyl acrylate and featuring the use of Fleming's one-pot procedure for the conversion of the phenyldimethylsilyl group to the hydroxyl as the salient, pivotal step in the synthesis.
