Asymmetric Synthesis of the C1–C13 Fragment of the Marine Metabolite Bistramide K

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.