The first report on the stereoselective synthesis of dysoxylactam A is disclosed. The five stereogenic centers of the fatty acid chain are created by utilizing Merck-Carreira and Marshall’s propargylation reaction, Evans’ alkylation methodology, and Noyori’s transfer hydrogenation protocol.

Two stereoselective routes to the C7–C22 subunit of amphidinolide K are disclosed. Jacobsen’s hydrolytic kinetic resolution and Sharpless’ asymmetric dihydroxylation reactions have been employed for the construction of the tetrahydrofuran ring. The C10–C11, C16–C17, C9–O, and C18–O bonds have been created using α-chloro sulfide intermediates and [2,3] sigmatropic rearrangement. Marshall’s propargylation protocol is utilized to create the C4 stereogenic center, and regioselective hydrozirconation/iodine quench afforded an alkenyl iodide which is employed in the NHK coupling with the C7–C22 subunit. Oxonia-Cope rearrangement resulted in the creation of the C18 carbinol stereogenic center and chain elongation.