Department of Chemistry and Chemical Biology, Northeastern University , Boston, Massachusetts 02115, United States.
Department of Chemistry, William Paterson University , 300 Pompton Road, Wayne, New Jersey 07470, United States.
Org Lett. 2016 Oct 7;18(19):4970-4973. doi: 10.1021/acs.orglett.6b02432. Epub 2016 Sep 16.
A de novo asymmetric total synthesis of the macrolide natural product (S)-phoracantholide J has been achieved in 10 steps from the commodity chemicals (1-pentyne, ethyl acrylate, acetaldehyde, and hydrogen). The asymmetry of the route was introduced by a Noyori reduction of a 3-yn-2-one, which makes the route equally amenable to the synthesis of either enantiomer. In addition, this route relies upon an alkyne zipper, a hydroalkynylation, and a macrolactonization to complete the synthesis.
从头不对称全合成大环内酯天然产物（S）-苦玄参内酯 J 已经从商品化学品（1-戊炔、丙烯酸乙酯、乙醛和氢气）实现了 10 步。该路线的不对称性是通过 3-炔-2-酮的 Noyori 还原引入的，这使得该路线同样适用于合成任一对映异构体。此外，该路线依赖炔烃拉链、氢炔基化和大环内酯化来完成合成。
