Asymmetric synthesis of a C1C19 fragment of ulapualide A

The stereocontrolled synthesis of a C1–C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsenʹs hydrolytic kinetic resolution (HKR) of a terminal epoxide, while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1C6 and the C7C19 fragments by a Kishi–Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment.