Department of Chemistry, Faculty of Science and Technology, Keio University , Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan.
J Org Chem. 2017 Jul 7;82(13):6770-6777. doi: 10.1021/acs.joc.7b00905. Epub 2017 Jun 14.
The first total synthesis of biselyngbyaside, an 18-membered macrolide glycoside, was achieved. The glycoside bond was introduced using the Schmidt method before construction of the 18-membered ring due to the instability of the conjugated diene and the β-hydroxy ester moiety. The macrolactone ring was constructed using the Mitsunobu reaction followed by intramolecular the Stille coupling reaction.
首次实现了 biselyngbyaside 的全合成，这是一种 18 元大环糖基内酯。由于共轭二烯和β-羟基酯部分的不稳定性，在构建 18 元环之前采用施密特（Schmidt）法引入糖苷键。通过 Mitsunobu 反应构建大环内酯环，然后进行分子内 Stille 偶联反应。
