SYNTHESIS OF ERYTHRINA AND RELATED ALKALOIDS .37. CHIRAL SYNTHESIS OF ENANTIO-TYPE ERYTHRINAN ALKALOIDS UTILIZING ASYMMETRIC ACYLATION AND KINETIC RESOLUTION OF DIASTEREOMERS

被引：18

作者：

HOSOI, S ^{[1
]}

ISHIDA, K ^{[1
]}

SANGAI, M ^{[1
]}

TSUDA, Y ^{[1
]}

机构：

[1] KANAZAWA UNIV, FAC PHARMACEUT SCI, 13-1 TAKARA MACHI, KANAZAWA, ISHIKAWA 920, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1992年 / 40卷 / 11期

关键词：

D O I：

10.1248/cpb.40.3115

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Chiral synthesis of an erythrinan alkaloid, (-)-3-demethoxyerythratidinone (11), as well as a versatile intermediate, the 1,7-cycloerythrinan derivative (14) (both are or enantio-type) was achieved using asymmetric acylation and kinetic resolution starting from the L-dopa derivative (1).

引用

页码：3115 / 3117

页数：3

共 26 条

[1] CHIRAL SYNTHESIS OF ERYTHRINA ALKALOIDS .2. SYNTHESIS OF ENANTIO-TYPE ERYTHRIAN ALKALOIDS UTILIZING ASYMMETRIC ACYLATION AND KINETIC RESOLUTION OF DIASTEREOMERS
TSUDA, Y
HOSOI, S
ISHIDA, K
SANGAI, M
CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (02) : 204 - 213
[2] Synthesis of Erythrina and related alkaloids part XLVII -: General method for synthesis of erythrinan and homoerythrinan alkaloids (1):: Synthesis of a cycloerythrinan, as a key intermediate to Erythrina alkaloids, by Pummerer-type reaction
Toda, J
Niimura, Y
Takeda, K
Sano, T
Tsuda, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1998, 46 (06) : 906 - 912
[3] DIOXOPYRROLINES .13. SYNTHESIS OF ERYTHRINA AND RELATED ALKALOIDS - A PRACTICAL ROUTE TO SPIRO-TYPE HETEROCYCLES RELATED TO ERYTHRINAN
TSUDA, Y
SAKAI, Y
KANEKO, M
ISHIGURO, Y
ISOBE, K
TAGA, J
SANO, T
HETEROCYCLES, 1981, 15 (01) : 431 - 436
[4] SYNTHESIS OF ERYTHRINA AND RELATED ALKALOIDS .18. SYNTHESIS OF COCCULOLIDINE SKELETON, A NONAROMATIC NOR-ERYTHRINAN ALKALOID
ISOBE, K
MOHRI, K
MAEDA, M
TAKEDA, T
TSUDA, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1987, 35 (06) : 2602 - 2604
[5] SYNTHESIS OF ERYTHRINA AND RELATED ALKALOIDS .12. DDQ OXIDATION OF SOME ERYTHRINAN ENONES AND DIENONES - SYNTHESES OF (+/-)-ERYTHARBINE AND (+/-)-CRYSTAMIDINE
TSUDA, Y
HOSOI, S
KIUCHI, F
SANO, T
TODA, J
YAMAMOTO, R
HETEROCYCLES, 1984, 22 (10) : 2255 - 2258
[6] Synthesis of erythrina and related alkaloids, Part 49 -: Synthesis of four possible stereoisomers of 1,2-epoxy-3-hydroxyerythrinans:: total synthesis of an alkenoid-type erythrinan alkaloid, (±)-erythratidine
Hosoi, S
Nagao, M
Tsuda, Y
Isobe, K
Sano, T
Ohta, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (10): : 1505 - 1511
[7] SYNTHESIS OF ERYTHRINA AND RELATED ALKALOIDS .22. INTRAMOLECULAR CYCLIZATION APPROACH .1. NEW SYNTHETIC ROUTE TO ERYTHRINAN AND RELATED HETEROCYCLES AND SYNTHESIS OF (+/-)-3-DEMETHOXYERYTHRATIDINONE
TSUDA, Y
SAKAI, Y
NAKAI, A
KANEKO, M
ISHIGURO, Y
ISOBE, K
TAGA, J
SANO, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (06) : 1462 - 1472
[8] ASYMMETRIC [2+2] PHOTOCYCLOADDITION REACTION OF A CHIRAL DIOXOPYRROLINE TO 2-(TRIMETHYLSILYLOXY)BUTADIENE - CHIRAL SYNTHESIS OF ERYTHRINA ALKALOIDS
SANO, T
KAMIKO, M
TODA, J
HOSOI, S
TSUDA, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (06) : 1373 - 1375
[9] Asymmetric synthesis of β,γ-unsaturated α-amino acids via efficient kinetic resolution with cinchona alkaloids
Hang, Jianfeng
Deng, Li
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (14) : 3856 - 3858
[10] Studies on the asymmetric synthesis of pyrrolidine alkaloids and related compounds(I) - synthesis of a chiral precursor for preussin and AHPPA
Huang, Pei-Qiang
Ruan, Yuan-Ping
Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities, 1995, 16 (12):

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