Olivanic acid analogues. Part 9. Allylic oxidative functionalisation of substituted azetidinones: synthesis of some 4-acyloxy-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylates
作者:John H. Bateson、Alison M. Robins、Robert Southgate
DOI:10.1039/p19910002399
日期:——
allylic alcohol 8 which was transformed to the 5,6-trans-4α-acetoxyolivanic acid derivative 16. Kharasch–Sosnovsky benzoyloxylation (PhCO3But, CuCl, PhH, heat) of the silylated 7-azabicyclo[4.2.0]oct-3-enes 17b,c provided inter alia allylic benzoates 18b,c and 21b,c. These were synthetic precursors of the 5,6-cis-olivanic acidanalogues 23 and 26, which contain 8- and 4α-benzoyloxy groups, respectively.
夏普勒斯氧化(卜吨Ò 2 H,的SeO 2)所述受保护的氮杂环丁酮烯丙基7,得到烯丙基醇8将其转化为5,6-反式-4α-acetoxyolivanic酸衍生物16。甲硅烷基化的7-氮杂双环[4.2.0] oct-3-enes 17b,c的Kharasch-Sosnovsky苯甲酰氧基化反应(PhCO 3 Bu t,CuCl,PhH,热)除其他外,还提供了烯丙基苯甲酸酯18b,c和21b,c。这些是5,6-顺式的合成前体-橄榄酸类似物23和26,其分别含有8和4α-苯甲酰氧基。
Bateson, John H.; Robins, Alison M.; Southgate, Robert, Journal of the Chemical Society. Perkin transactions I, 1991, # 1, p. 29 - 35
作者:Bateson, John H.、Robins, Alison M.、Southgate, Robert