Department of Chemistry, Drexel University, 32 South 32nd Street Philadelphia, Pennsylvania 19104, United States.
Wistar Institute, 3601 Spruce Street, Philadelphia, Pennsylvania 19104, United States.
Org Lett. 2021 Feb 19;23(4):1500-1503. doi: 10.1021/acs.orglett.1c00288. Epub 2021 Feb 3.
Oxazoles are rapidly assembled through a sequential deprotonation-condensation of Asmic, anisylsulfanylmethylisocyanide, with esters followed by sulfanyl-lithium exchange-trapping. Deprotonating Asmic affords a metalated isocyanide that efficiently traps esters to afford oxazoles bearing a versatile C-4 anisylsulfanyl substituent. Interchange of the anisylsulfanyl substituent is readily achieved through a first-in-class sulfur-lithium exchange-electrophilic trapping sequence whose versatility is illustrated in the three-step synthesis of the bioactive natural product streptochlorin.
通过 Asmic、茴香硫基甲基异氰酸酯、酯的连续去质子化-缩合，然后进行硫基-锂交换-捕获，可以快速合成噁唑。去质子化 Asmic 生成一个金属化的异氰酸酯，有效地捕获酯，得到含有多功能 C-4 茴香硫基取代基的噁唑。通过一流的硫-锂交换-亲电捕获序列可以很容易地实现茴香硫基取代基的交换，该序列的多功能性在生物活性天然产物streptochlorin 的三步合成中得到了说明。
