112342-35-5Relevant academic research and scientific papers
Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans
Padwa, Albert,Wang, Qiu
, p. 7391 - 7402 (2006)
Several 2-imido substituted furans were found to undergo a rapid intramolecular [4 + 2]-cycloaddition to deliver oxabicyclo adducts in good to excellent yields. By using a Rh(I)-catalyzed ring opening of the resulting oxabicyclic adduct, it was possible t
Efficient synthesis of (+/-)-erysotramidine using an NBS-promoted cyclization reaction of a hexahydroindolinone derivative.
Lee, Hyoung Ik,Cassidy, Michael P,Rashatasakhon, Paitoon,Padwa, Albert
, p. 5067 - 5070 (2003)
An NBS-promoted intramolecular electrophilic aromatic substitution reaction of a hexahydroindolinone derivative was used to assemble the tetracyclic core of the erythrinane skeleton. The resulting cyclized product was transformed into (+/-)-erysotramidine
Synthesis of the erythrina alkaloid erysotramidine
L'Homme, Chloé,Ménard, Marc-André,Canesi, Sylvain
, p. 8481 - 8485 (2015/03/18)
A concise synthesis of erysotramidine (an alkaloid belonging to the erythrina family) was achieved starting with an inexpensive phenol and amine derivative. The synthesis is based on oxidative phenol dearomatizations mediated by a hypervalent iodine reage
General and efficient strategy for erythrinan and homoerythrinan alkaloids: Syntheses of (±)-3-demethoxyerythratidinone and (±)- erysotramidine
Gao, Shuanhu,Tu, Yong Qiang,Hu, Xiangdong,Wang, Shaohua,Hua, Rongbao,Jiang, Yijun,Zhao, Yuming,Fan, Xiaohui,Zhang, Shuyu
, p. 2373 - 2376 (2007/10/03)
A general and efficient strategy to both aromatic-type and nonaromatic-type erythrinan and homoerythrinan alkaloids has been developed. This approach involves a key two-step sequence, an alkylation of a ketone with various N-substituted iodoacetamides fol
Electrophilic-induced cyclization reaction of hexahydroindolinone derivatives and its application toward the synthesis of (±)- erysotramidine
Padwa, Albert,Lee, Hyoung Ik,Rashatasakhon, Paitoon,Rose, Mickea
, p. 8209 - 8218 (2007/10/03)
A convenient synthesis of variously substituted octahydroindolo[7a,1a]- isoquinolinones has been achieved by an acid-induced cyclization of hexahydroindolinones bearing tethered phenethyl groups. The formation of a single lactam diastereomer is the result
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
Synthesis of Erythrina and related alkaloids. XXIV. Total synthesis of erysotrine from 1,7-cycloerythrinan derivatives by the use of a new 1,2-carbonyl transposition method
Tsuda,Hosoi,Nakai,Sakai,Abe,Ishi,Kiuchi,Sano
, p. 1365 - 1373 (2007/10/02)
Treatment of 2,8-dioxo-1,7-cycloerythrinans with phenylselenenyl chloride in the presence of BF3·Et2O as a catalyst gave 3-chloro-3-phenylselenenyl derivatives through the 3-phenylselenenyl derivative, which changed into the Δ3
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.
