The Journal of organic chemistry

Synthesis of prostaglandin synthetase substrate analogs. 1.(Z)-14-Hydroxy-12, 13-methano-8-nonadecenoic acid

MI Dawson, M Vasser

文献索引：Dawson,M.I.; Vasser,M. Journal of Organic Chemistry, 1977 , vol. 42, p. 2783 - 2785

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被引用次数: 31

摘要

Wittig reaction of 4-benzyloxybutanal (1) with the ylide derived from treatment of 7- carboxyheptyltriphenylphos-phonium bromide with sodio methylsulfinylmethide in dimethyl sulfoxide afforded (2)-12-benzyloxy-8-dodecenoic acid (2) in 87% yield. Reduction of benzyl ether 2 with sodium in liquid ammonia-tetrahydrofuran, followed by esterification, provided a 74% yield of methyl (2)-12-hydroxy-8-dodecenoate (4). None of the E isomer was ...