An expedient route to the calabar bean alkaloids (-)-physovenine and (-)-physostigmine

被引：60

作者：

El-Azab, AS ^{[1
]}

Taniguchi, T ^{[1
]}

Ogasawara, K ^{[1
]}

机构：

[1] Tohoku Univ, Inst Pharmaceut, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 18期

关键词：

D O I：

10.1021/ol006065o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expedient route to the Calabar bean alkaloids (-)-physovenine and (-)-physostigmine has been devised using a chiral building block which was originally designed for diastereocontrolled construction of aldohexoses.

引用

页码：2757 / 2759

页数：3

共 19 条

[1] IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids:: Asymmetric synthesis of (+)-luciduline [J].

Comins, DL ;

Brooks, CA ;

Al-awar, RS ;

Goehring, RR .

ORGANIC LETTERS, 1999, 1 (02) :229-231

[2]

COXWORTH E, 1967, ALKALOIDS, V10, P383

[3] An efficient synthesis of optically active physostigmine from tryptophan via alkylative cyclization [J].

Kawahara, M ;

Nishida, A ;

Nakagawa, M .

ORGANIC LETTERS, 2000, 2 (05) :675-678

[4]

MARION L, 1952, ALKALOIDS, V2, P438

[5] Catalytic asymmetric synthesis of either enantiomer of the Calabar alkaloids physostigmine and physovenine [J].

Matsuura, T ;

Overman, LE ;

Poon, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6500-6503

[6]

ROBINSON B, 1971, ALKALOIDS, V13, P213

[7] GENERAL PROCEDURE FOR SYNTHESIS OF MONO-N-ACYLATED 1,6-DIAMINOHEXANES [J].

STAHL, GL ;

WALTER, R ;

SMITH, CW .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (11) :2285-2286

[8]

SUGINOME H, 1970, TETRAHEDRON LETT, P4571

[9]

TAKANO S, 1982, CHEM PHARM BULL, V30, P2641

[10] ENANTIOCONTROLLED TOTAL SYNTHESES OF (-)-PHYSOVENINE AND (-)-PHYSOSTIGMINE [J].

TAKANO, S ;

MORIYA, M ;

OGASAWARA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :5982-5984

← 1 2 →