70635-23-3Relevant academic research and scientific papers
Stereoselective introduction of oxygen functionalities at the 11β- position of erythrinan skeleton: Total syntheses of (±)-erythristemine and (+)-erythrartine
Isobe,Mohri,Takeda,Suzuki,Hosoi,Tsuda
, p. 197 - 203 (1994)
Oxidation of 8-oxoerythrinan and 8-oxo-1,7-cycloerythrinan derivatives with 2 mol eq of ceric ammonium nitrate in alcohols or acetic acid gave the corresponding 11β-alkoxy or acetoxy compounds in moderate yield. Thus, (±)- 3,3,15,16-tetramethoxy-1,7-cycloerythrinan-2,8-dione and (+)-erysotramidine gave the corresponding 11β-methoxy and 11β-acetoxy derivatives on oxidation in methanol and in acetic acid, respectively. Those compounds were respectively converted into (±)-erythristemine and (+)-erythrartine in several steps, thus achieving the total synthesis of these alkaloids.
Synthesis of four possible stereoisomers of 1,2-epoxy-3-hydroxy-erythrinans: Total synthesis of an alkenoid-type erythrinan alkaloid, (±)-erythratidine
Hosoi, Shinzo,Nagao, Motoyoshi,Tsuda, Yoshisuke,Isobe, Kimiaki,Sano, Takehiro,Ohta, Tomihisa
, p. 1505 - 1511 (2007/10/03)
Four stereoisomers of 1,2-epoxy-3-hydroxyerythrinans were synthesized and their stereochemistries were determined. The 1,2α-epoxy-3α-alcohol was converted to the alkenoid-type alkaloid, (±)-erythratidine utilizing reductive migration of an α, β-unsaturate
Chiral synthesis of Erythrina alkaloids. I. Total synthesis of (+)-erysotrine via asymmetric Diels-Alder reaction under high pressure
Tsuda,Hosoi,Katagiri,Kaneko,Sano
, p. 2087 - 2095 (2007/10/02)
(S)-(+)-3,4-Dimethoxyphenylalanine methyl ester (1b) was converted, in 3 steps, into (5S)-(-)-8,9-dimethoxy-1,5-dimethoxycarbonyl-2,3-dioxo-2,3,5,6-tetrahy dropyrrolo[2,1-a]isoquinoline (2b). Diels-Alder reaction of 2b with 1-methoxy-3-trimethylsilyloxybu
TOTAL SYNTHESIS OF (+)-ERYSOTRINE VIA ASYMMETRIC DIELS-ALDER REACTION UNDER SUPER HIGH PRESSURE
Tsuda, Yoshisuke,Hosoi, Shinzo,Katagiri, Nobuya,Kaneko, Chikara,Sano, Takehiro
, p. 497 - 502 (2007/10/02)
The first total synthesis of (+)-erysotrine in a chiral form was achieved through application of Diels-Alder reaction of a chiral dioxopyrroline with 1-methoxy-3-trimethylsilyloxybutadiene under a 10 Kbar pressure.
SYNTHESIS OF 11β-HYDROXY ERYTHRINA ALKALOID, ERYTHRARTINE, AND ITS O-ACETATE (ERYTHRASCINE?)
Isobe, Kimiaki,Mohri, Kunihiko,Suzuki, Kazumi,Haruna, Mitumasa,Ito, Kazuo,et al.
, p. 1195 - 1198 (2007/10/02)
Oxidation of an erythrinan alkaloid erysotramidine (4) with CAN in AcOH-MeCN gave, in moderate yield, the 11β-acetoxy derivative (5b), which was transformed into erythrartine (8).Its O-acetate (O-acetylerythrartine) was not identical with erythrascine in the 1H-nmr spectra, presenting an ambiguity on the reported structure of erythrascine.
CONFORMATIONAL DIFFERENCE BETWEEN ERYTHRINAN- AND HOMOERYTHRINAN-3-ONES: TOTAL SYNTHESIS OF (+/-)-SCHELHAMMERIDINE AND (+/-)-3-EPISCHELHAMMERIDINE
Tsuda, Yoshisuke,Hosoi, Shinzo,Murata, Masami
, p. 311 - 316 (2007/10/02)
Erythrinan- and homoerythrinan-3-ones behave differently toward hydride reductions suggesting their conformational difference: for example, Δ1-erythrinan-3-one gives 3α-alcohol and Δ1-homoerythrinan-3-one gives 3β-alcohol stereoselectively on reduction with NaBH4-CeCl3 in methanol.Based on these observations, total syntheses of homoerythrinan alkaloids, schelhammeridine and 3-epischelhammeridine, and an erythrinan alkaloid, 8-oxoerysotrine, were accomplished.
SYNTHESES OF ERYTHRINA AND RELATED ALKALOIDS (6) TOTAL SYNTHESIS OF ERYSOTRINE AND ERYTHRALINE
Sano, Takehiro,Toda, Jun,Tsuda, Yoshisuke
, p. 229 - 232 (2007/10/02)
An efficiently stereocontrolled synthesis of the erythrina alkaloids, erysotrine and erythraline was described.
