A novel and efficient total synthesis of (±)-physostigmine

被引:29
作者
Kulkarni, Mukund G. [1 ]
Dhondge, Attrimuni P. [1 ]
Borhade, Ajit S. [1 ]
Gaikwad, Dnyaneshwar D. [1 ]
Chavhan, Sanjay W. [1 ]
Shaikh, Yunnus B. [1 ]
Ningdale, Vijay B. [1 ]
Desai, Mayur P. [1 ]
Birhade, Deekshaputra R. [1 ]
Shinde, Mahadev P. [1 ]
机构
[1] Univ Pune, Dept Chem, Pune 411007, Maharashtra, India
关键词
CATALYTIC ASYMMETRIC-SYNTHESIS; QUATERNARY CARBON CENTERS; INTRAMOLECULAR HECK REACTIONS; FORMAL TOTAL-SYNTHESIS; PRACTICAL TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC-SUBSTITUTION; ABSOLUTE-CONFIGURATION; CALABAR ALKALOIDS; INDOLE SERIES;
D O I
10.1016/j.tetlet.2009.03.012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Application of the Wittig olefination-Claisen rearrangement protocol for the total synthesis of (+/-)-physostigmine. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2411 / 2413
页数:3
相关论文
共 122 条
[91]   CONFORMATIONAL AND MOLECULAR STUDY OF THE 4-(2-CARBOXYETHYL)-1,2,3,4-TETRAHYDROCYCLOPENT[B]INDOLE [J].
RODRIGUEZ, JG ;
TEMPRANO, F ;
ESTEBANCALDERON, C ;
MARTINEZRIPOLL, M ;
GARCIABLANCO, S .
TETRAHEDRON, 1985, 41 (18) :3813-3823
[92]   Total synthesis of isoroquefortine C [J].
Schiavi, BM ;
Richard, DJ ;
Joullié, MM .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (03) :620-624
[93]   FRAGMENTATION OF OPTICALLY-ACTIVE (1-PHENYLETHYL)UREA AND (1-NAPHTHYLETHYL)UREA IN REFLUXING ALCOHOLS - EASY PREPARATION OF OPTICALLY-ACTIVE AMINES OF HIGH OPTICAL PURITY [J].
SCHONENBERGER, B ;
BROSSI, A .
HELVETICA CHIMICA ACTA, 1986, 69 (06) :1486-1497
[94]   From ordeal poison to Alzheimer's therapy [J].
Sneader, W .
DRUG NEWS & PERSPECTIVES, 1999, 12 (07) :433-437
[95]   Nucleophilic substitution reaction on the nitrogen of indole nucleus: Formation of 1-(indol-3-yl)indole upon reaction of 1-hydroxyindoles with indole in formic acid [J].
Somei, M ;
Yamada, F ;
Hayashi, T ;
Goto, A ;
Saga, Y .
HETEROCYCLES, 2001, 55 (03) :457-460
[96]   The chemistry of indoles part 91 -: Preparations of melatonin and 1-hydroxymelatonin, and its novel nucleophilic dimerization to (±)-3a,3a′-bispyrrolo[2,3-b]indoles [J].
Somei, M ;
Oshikiri, N ;
Hasegawa, M ;
Yamada, F .
HETEROCYCLES, 1999, 51 (06) :1237-+
[97]   Physostigmine (Eserine). Part III. [J].
Stedman, E ;
Barger, G .
JOURNAL OF THE CHEMICAL SOCIETY, 1925, 127 :247-258
[98]   Total synthesis of (-)-physovenine from (-)-3a-hydroxyfuroindoline [J].
Sunazuka, T ;
Yoshida, K ;
Kojima, N ;
Shirahata, T ;
Hirose, T ;
Handa, M ;
Yamamoto, D ;
Harigaya, Y ;
Kuwajima, I ;
Omura, S .
TETRAHEDRON LETTERS, 2005, 46 (09) :1459-1461
[99]  
TAKANO S, 1982, CHEM PHARM BULL, V30, P2641
[100]   ENANTIOCONTROLLED TOTAL SYNTHESES OF (-)-PHYSOVENINE AND (-)-PHYSOSTIGMINE [J].
TAKANO, S ;
MORIYA, M ;
OGASAWARA, K .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :5982-5984