Heck Coupling Using a Vinyliodo-MIDA Boronate: An Efficient and Modular Access to Polyene Frameworks

A simple Heck coupling between an alkenyl iodo-boronate and a variety of terminal olefins is disclosed. This method gives access to a wide range of dienic moieties including valuable bis-functionalized dienes. The synthetic potential of the coupling reaction is demonstrated by a short and modular preparation of several tetraenic compounds

Synthetic Studies toward the C14–C29 Fragment of Mirabalin

A convergent synthesis of one isomer of the C14–C29 fragment of mirabalin is disclosed. The key steps include a Marshall allenylation, a Mukaiyama aldol reaction and a Crimmins aldolization, which allow the control of 10 out of 25 stereogenic centers present in the molecule

Synthetic Strategy toward the C44–C65 Fragment of Mirabalin

A convergent and flexible stereoselective synthesis of one isomer of the C44–C65 fragment of mirabalin is described. The key steps include organocatalytic aldolization, ruthenium-catalyzed asymmetric hydrogenation, amide formation, Marshall stereoselective allenylation, and the Nozaki–Hiyama–Kishi reaction