Department of Chemistry , Massachusetts Institute of Technology , 77 Massachusetts Avenue , Cambridge , Massachusetts 02139 , United States.
Org Lett. 2019 May 17;21(10):3606-3609. doi: 10.1021/acs.orglett.9b01019. Epub 2019 May 2.
Skipped polyenes featuring high ( E)-selectivity and varying methyl substitution patterns are synthesized using a nickel-catalyzed cross-coupling reaction between allyl trifluoroacetates and vinyl bromides. The utility of this cross-electrophile coupling is showcased in part by the synthesis of the RST fragment of the marine ladder polyether, maitotoxin. Construction of this fragment is particularly challenging due to the alternating methyl substitution pattern.
使用镍催化的烯丙基三氟乙酸酯和溴代乙烯的交叉偶联反应，合成了具有高（E）选择性和不同甲基取代模式的 skipped 多烯。该交叉电亲核试剂偶联的实用性部分体现在海洋梯型聚醚 maitotoxin 的 RST 片段的合成中。由于交替的甲基取代模式，该片段的构建极具挑战性。
