Shinzo Kano

A new facile diastereoconversion of 2-amino alcohols involving a novel cyclocarbamation

Abstract A new practical method for diastereoconversion of 2-amino alcohols was performed by treatment of N-Cbz- derivatives with trifluoromethanesulfonic anhydride or thionyl chloride, followed by ring cleavage of the resulting oxazolidin-2-ones

Stereocontrolled convergent synthesis of hydroxyethylene dipeptide isosteres by the reaction of α-amino aldehyde with alkoxytitanium homoenolates

Abstract The reaction of (S)-α-dibenzylamino aldehydes with dichloroisopropoxytitanium ester homoenolates gave the corresponding γ-aminoalkyl γ-lactones with high erythro selectivity. The same reaction by the use of amide homoenolates also afforded the corresponding 2-amino alcohols with high erythro-selectivity.

A Synthesis of Heterocyclic Fused Isoquinolines Through N-Acyliminium Ion Intermediates

Abstract Conversion of terminal olefin to formyl group by ozonolysis was applied to a new generation of N-acyliminium ions and several kinds of heterocyclic fused isoquinolines were prepared.

Diastereoselective synthesis of 2,6-disubstituted 3-hydroxy piperidine derivatives by an application of radical cyclization

N-[α-(2-bromo-1-butenyl)-α-methyl]oxazolin-2-one (7) and N-[α-(2-bromo-1-butenyl)-α-pyranyloxyethyl]oxazolin-2-one (14), obtained by starting with ethyl acetoacetate, were treated with tributyltin hydride in the presence of AIBN afforded the cyclisation products (8) and (15),respectively, with high diastereoselectivity

A new synthetic approach to (+)-galantinic acid, degradation product from the peptide antibiotic galantin. I: Via 4-amino-3-hydroxypyranose

5-Phenylthiooxazolidin-2-ones, derived from L-serine, were subjected to photo-induced radical allylation to give the corresponding 4-substituted 4,5-trans-5-allyloxazolidin-2-ones. 4-Ethoxyethyl derivative was led to N-Boc galant galantinic acid methyl ester via N-Boc 4-amino-3-hydroxypyranose

An efficient diastereoselective synthesis of 6-hydroxy-4a-[3,4-crowned(15-crown-5)phenyl]-trans-decahydroisoquinoline

Abstract A high diastereoselective synthesis of 6-hydroxy-4a-aryl- trans -decahydroisoquinoline derivatives was achieved by an application of N-acyliminium ion-induced polyene cyclization procedure.

Diastereoselective Synthesis of 2,6-Disubstituted 3-Hydroxypiperidine, 2-(a-Hydroxyalkyl)-3-hydroxypiperidine and 2-(a-Hydroxyalkyl)-3-hydroxypyrrolidine Derivatives

Reduction of 5-substituted 5,8a-trans-oxazolo[3,4-a]pyridin-8-ones (7a,b), obtained by an application of α-acylamino radical cyclization at the initial stage, with NaBH 4 and K-Selectride was found to proceed with complete stereocontrol in all cases

Formation of alcohols from alkenes with TiCl4–NaBH4

The reaction of alkenes with TiCl4–NaBH4 in 1,2-dimethoxyethane afforded alcohols, the hydroxy group of which was introduced in an anti-Markovnikov direction.

Highly diastereoselective synthesis of N-Boc dolaisoleuine, unusual amino acid in dolastatin 10

Photolysis of 5-phenylthiooxazolidin-2-one (4) in the presence of (n-Bu 3 Sn) 2 and n-Bu 3 SnCH 2 CH=CH 2 afforded 5-allyl derivative (5) which was led to N-Boc dolaisoleuine (11), one component of dolastatine 10 (2), via 6-10

A facile and efficient stereoselective synthesis of 6-hydroxy-trans-4a-phenyldecahydroisoquinoline

Abstract A stereoselective synthesis of 6-oxygenated trans -4a-phenyldecahydroisoquinoline was achieved by treatment of 1-ethoxycarbamoyl-1-phenyl-1,4-hexadiene with paraformaldehyde in formic acid.