Noritaka Chida

Stereoselective total synthesis of (+)-lycoricidine

Abstract The stereoselective total synthesis of the title compound starting from D-glucose is described. The key steps in this synthesis are Ferrier rearrangement to construct the optically active cyclohexenone (C-ring), and Pd-catalyzed intramolecular Heck reaction to build the phenanthridone skeleton.

Total synthesis of bengamide E

The first total synthesis of bengamide E (1), a novel sponge-derived amino acid, is described. The side chain of bengamide E (2) possessing four contiguous chiral centers was prepared in a stereoselective manner starting from naturally abundant cyclitol, l-quebrachitol.

Regioselective Baeyer-Villiger reaction of polyhydroxycyclohexanone derivatives

Abstract The regioselectivities observed in Baeyer-Villiger reaction of polyhydroxycyclohexanone derivatives possessing various substituents at adjacent carbons to the ketone carbonyl are reported. This study suggested that the trend of the migratory aptitude of substituted carbons would be a carbon with benzyloxy > methoxy > ketal oxygen ⪢ acyloxy ∼ methyl.

Total synthesis and absolute configuration of bengamide A

The first total synthesis of the novel marine natural product, bengamide A 1 is described, revealing the absolute configuration of this compound.

Total synthesis of hygromycin A

The first complete synthesis of antibiotic hygromycin A is reported; coupling of the protected sugar moiety (2) and the aminocyclitol (3) derived from D-glucose as the optically active from, followed by deprotection, gives the product (1) which was identified with an aunthentic sample by 400 MHz 1H n.m.r. spectroscopy.

Total synthesis and absolute configuration of FR65814

The chiral and highly stereoselective synthesis of FR65814 1, a novel immunosuppressant, starting from D-glucose is described; this first total synthesis fully confirms the proposed structure of 1.

Total synthesis of simmondsin

The first total synthesis of the naturally occurring cyanoglucoside, simmondsin 1, starting from L-quebrachitol and D-glucose, is described, revealing the absolute configuration of this compound.