Mitsutoshi Yanagiya

Stereocontrolled total synthesis of (+)-pederine

Abstract A mild one-pot method for the synthesis of acyclic N-(1-methoxyalkyl)amides starting from carboxylic acid and methyl imidates has been developed and applied to the first total synthesis of (+)-pederine (1), a potent insect poison. Furthermore, the stereocontrolled total synthesis of 1 was also achieved by employing acid catalyzed double alkoxy-exchange reaction of N-(1 -methoxylakyl)amide group as key step.

Chemical constitution of safflor yellow B. A quinochalcone C-glycoside from the flower petals of Carthamus tinctorius L.

Abstract The chemical constitution of safflor yellow B, a quinochalcone glycoside from the flower petals of Carthamus tinctorius L , has been characterized as 1, mainly on the basis of spectral means.

A simple method for synthesis of amides and peptides through acyl chlorides : A rapid synthesis of thyrotropin releasing hormone

Abstract By improvement of the classical SOCl 2 -pyridine method for the preparation of acid chlorides, amides and optically pure peptides were synthesized rapidly in a simple manner from DCHA dicyclohexylammonium) salts of carboxylic acids. This modified SOCl 2 -pyridine method was applied to a rapid synthesis of TRH.

Remote acyclic stereocontrol. Chiral synthesis of (+)-pedamide

Abstract Synthesis of optically active pedamide (3), one of the tetrahydropyran moieties of the potent insect poison pederine (1), has been accomplished through a new, remote controlled asymmetric reduction of a ketone as key step.

Effective deprotection of 2-(trimethylsilylethoxy)methylated alcohols (SEM ethers). Synthesis of thyrsiferyl-23 acetate

Abstract New conditions for effective cleavage of SEM ethers were developed (TBAF/HMPA in the presence of MS 4A) and usefulness of this reaction was demonstrated by the synthesis of thyrsiferyl-23 acetate.

Total synthesis of (+)-pedamide. A new, remote controlled asymmetric induction

Abstract Total synthesis of optically active pedamide 2 , one of the tetrahydropyran moieties of the potent insect poison pederine 1 , was achieved by employing a new, remote controlled asymmetric reduction of a ketone as key step.

A new synthesis of d1-coriolin A. Application of a new SN2 reaction at a neopentylic position

Abstract Dicyclopentadiene has been stereoselectively converted to a key tricyclic intermediate for the total synthesis of coriolin, through a route which involves a new S N 2 reaction at a neopentylic position.

Synthesis of A-B-C-ring segment of thyrsiferol construction of a strained tetrahydropyran ring existent as a boat form

Abstract Tricyclic bromoether 17 , which contained twenty of thirty carbons of thyrsiferol ( 1d ), was synthesized in optically active form starting from trivial compounds 2 and 3 .

Total synthesis of (+)-thyrsiferol and (+)-venustatriol

Abstract Triterpenoid polyethers (+)-thyrsiferol ( 1a ) and (+)-venustatriol ( 1d ) were totally synthesized from trivial compounds.

Total synthesis of (+)-pederine. A simple synthetic method for N-(1-methoxyalkyl)amides

Abstract A mild one-pot method for the synthesis of acyclic N-(1-methoxyalkyl)amides starting from carboxylic acids and methyl imidates had been developed and applied to the total synthesis of the insect poison pederine 1 .