立体选择性合成arenicolides A 和 B 的 C(25)-C(36)片段：三取代环氧化物的构型确定。
Stereoselective synthesis of the C(25)-C(36) segment of arenicolides A and B: determination of the configuration of the trisubstituted epoxide.
机构信息
Department of Applied Chemistry, Kogakuin University, Nakano 2665-1, Hachioji, Tokyo 192-0015, Japan.
出版信息
Org Lett. 2010 Mar 5;12(5):908-11. doi: 10.1021/ol902750e.
Two diastereomeric epoxides 4a and 4b corresponding to the C(25)-C(36) fragment of arenicolides A and B were synthesized in a stereoselective manner involving the Pd(0)-catalyzed stereospecific methoxy substitution reaction of epoxy unsaturated ester 6 with B(OMe)(3) as the key step. Comparison of the (1)H NMR spectra of the synthetic compounds with that of arenicolide A revealed that the configuration of the epoxide in arenicolides A and B is 30R and 31R.
两种非对映环氧 4a 和 4b 对应于阿雷尼科利德 A 和 B 的 C(25)-C(36) 片段，以 Pd(0)-催化的环氧不饱和酯 6 与 B(OMe)(3) 的立体特异性甲氧基取代反应为关键步骤，以立体选择性方式合成。将合成化合物的 (1)H NMR 谱与阿雷尼科利德 A 的 (1)H NMR 谱进行比较，表明阿雷尼科利德 A 和 B 中环氧化物的构型为 30R 和 31R。
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