Asymmetric synthesis of the C1-C13 fragment of the marine metabolite bistramide K

摘要

A synthetic study on the construction of the C1-C13 fragment of bistramide K is described. This unit differs from other members of the bistramide family, which are equipped with a pyran structure at C6-C11. In bistramide K, the linear C1-C13 portion contains three stereogenic centers as well as two supplementary (E)-olefin positions. The key step in the synthesis was the elaboration of the (E)-olefin C6-C7 by using a Julia-Kocienski reaction between aldehyde 4 and benzothiazolesulfone 15. A synthesis of the C1-C13 fragment of the natural bistramide K is described.