A formal synthesis of (+)-α-allokainic acid via sulfanyl radical addition-cyclization reaction

被引：0

作者：

Miyata, O ^{[1
]}

Ozawa, Y

Ninomiya, T

Aoe, K

Hiramatsu, H

Naito, T

机构：

[1] Kobe Pharmaceut Univ, Kobe, Hyogo 658, Japan

[2] Tanabe Seiyaku Co Ltd, Analyt Res Lab, Yodogawa Ku, Osaka 532, Japan

来源：

HETEROCYCLES | 1997年 / 46卷

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfanyl radical addition-cyclization of the diallylamines in the presence of thiophenol and AIBN gave the 2,3,4-trisubstituted pyrrolidines which were effectively converted into the known key intermediate for the synthesis of (+)-alpha-allokainic acid via conversion of the phenylsulfanylmethyl group into the isopropenyl group at the 4-position.

引用

收藏

页码：321 / 333

页数：13

相关论文

共 14 条

[1] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS [J].

BECKWITH, ALJ .

TETRAHEDRON, 1981, 37 (18) :3073-3100

[2] Stereoselective synthesis of (-)-alpha-kainic acid and (+)-alpha-allokainic acid via trimethylstannyl-mediated radical carbocyclization and oxidative destannylation [J].

Hanessian, S ;

Ninkovic, S .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5418-5424

[3] SYNTHESIS OF CONFORMATIONALLY RESTRICTED ANALOGS OF KAINIC ACID - IS THE CONFORMATION OF THE C4-SUBSTITUENT OF KAINOID IMPORTANT TO ITS NEUROEXCITATORY ACTIVITY [J].

HASHIMOTO, K ;

OHFUNE, Y ;

SHIRAHAMA, H .

TETRAHEDRON LETTERS, 1995, 36 (35) :6235-6238

[4] STEREOCONTROLLED CONSTRUCTION OF SUBSTITUTED PYRROLIDINES BASED ON INTRAMOLECULAR PROTODESILYLATION REACTION - ENANTIOSPECIFIC SYNTHESIS OF (-)-KAINIC ACID AND (+)-ALLOKAINIC ACID FROM L-SERINE [J].

HATAKEYAMA, S ;

SUGAWARA, K ;

TAKANO, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :125-127

[5] CARBON CARBON BOND-FORMING REACTIONS USING CERIUM METAL OR ORGANOCERIUM(III) REAGENTS [J].

IMAMOTO, T ;

KUSUMOTO, T ;

TAWARAYAMA, Y ;

SUGIURA, Y ;

MITA, T ;

HATANAKA, Y ;

YOKOYAMA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :3904-3912

[6] DIASTEREOSELECTIVE SYNTHESIS OF GAMMA-HYDROXY-BETA-AMINO ALCOHOLS, (2S,3S)-THREONINOL AND (2S,3R)-THREONINOL AND (2S,3R)-HYDROXYPHENYLALANINOL, FROM (R)-GLYCIDOL VIA THE DERIVED 4-HYDROXYMETHYLOXAZOLIDINONE [J].

KATSUMURA, S ;

YAMAMOTO, N ;

MORITA, M ;

HAN, QJ .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :161-164

[7]

KRAUSE HJ, 1966, Patent No. 1226554

[8] Hydroximate as a synthetically useful functional group: A novel synthesis of lactones using hydroximates as a tether [J].

Miyata, O ;

Nishiguchi, A ;

Ninomiya, I ;

Naito, T ;

Aoe, K ;

Okamura, K .

TETRAHEDRON LETTERS, 1996, 37 (02) :229-232

[9]

Miyata O, 1996, CHEM PHARM BULL, V44, P1285

[10]

MIYATA O, 1997, IN PRESS SYNLETT