Mitsuaki Ide

Smooth Isoindolinone Formation from Isopropyl Carbamates via Bischler–Napieralski-Type Cyclization

Isopropyl carbamates derived from benzylamines provide isoindolinones by treatment with phosphorus pentoxide at room temperature. Utility of this Bischler-Napieralski-type cyclization and a new mechanism involving a carbamoyl cation for rationalization of this smooth conversion are discussed.

Synthetic studies on lactonamycins: synthesis of the model BCDEF aglycon.

The lactonamycin model aglycon 4 was synthesized from the trihalogenated benzene derivative 10. Ethynyltetraol 6 was prepared from 10 via carbon elongations, oxidative demethylation, a cycloaddition reaction with the diene derived from homophthalic anhydride, and dihydroxylation. Final E- and F-ring constructions from 6 were realized via a palladium-catalyzed cyclization-methoxycarbonylation, a stereoselective methanol addition, and lactonization, leading to the production of 4.

Synthesis of the C15-C27 portion of venturicidins: A formal total synthesis of venturicidin X

Abstract The C15–C27 portion of venturicidin X was prepared using substitution reactions of alkyl trifluoromethanesulfonates with a vinylmetal compound followed by homogeneous hydrogenation. Together with our previous synthesis of the C1–C14 portion of venturicidin X, a formal total synthesis of venturicidin X was completed.

Practical deracemization of NM-3, a synthetic angiogenesis inhibitor

The practical deracemization of the angiogenesis inhibitor NM-3 is described. The transformation features the diastereoselective addition of optically active pantolactone to a ketene intermediate and hydrolysis of the pantolactone ester.