General strategy for the construction of enantiopure pyrrolidine-based alkaloids. Total synthesis of (-)-monomorine

被引：31

作者：

Zhang, Suhong ^{[1
]}

Xu, Liang ^{[1
]}

Miao, Lei ^{[1
]}

Shu, Hong ^{[1
]}

Trudell, Mark L. ^{[1
]}

机构：

[1] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 08期

关键词：

D O I：

10.1021/jo062532p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantiopure cis-2,5-disubstituted pyrrolidine building block was prepared from cocaine. The synthetic utility of this compound as a chiral building block was demonstrated by a short and efficient synthesis of the pyrrolidine-based alkaloid (-)-monomorine (six steps, 37% overall yield).

引用

页码：3133 / 3136

页数：4

共 50 条

[1] ORGN 123-General strategies for the enantioslective construction of pyrrolidine-based alkaloids: Total synthesis of (+)-cis-pyrrolidine 225H
Noble, April
Trudell, Mark L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
[2] General strategy for the synthesis of Strychnos alkaloids.
He, SW
Rawal, VH
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U208 - U209
[3] A GENERAL-ROUTE FOR THE SYNTHESIS OF ENANTIOPURE INDOLIZIDINE ALKALOIDS FROM ALPHA-AMINO-ACIDS - TOTAL SYNTHESIS OF (+)-MONOMORINE
ANGLE, SR
BREITENBUCHER, JG
TETRAHEDRON LETTERS, 1993, 34 (25) : 3985 - 3988
[4] Total synthesis of the bioactive marine alkaloids.
Poullennec, KG
Romo, D
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U180 - U180
[5] Approaches to the total synthesis of stemona alkaloids.
Subramanian, T
Sibi, MP
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U352 - U352
[6] Progress in the total synthesis of stemona alkaloids.
Wipf, P
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U458 - U458
[7] Synthesis of D-arabinose-derived polyhydroxylated pyrrolidine, indolizidine and pyrrolizidine alkaloids. Total synthesis of hyacinthacine A2
Delso, Ignacio
Tejero, Tomas
Goti, Andrea
Merino, Pedro
TETRAHEDRON, 2010, 66 (06) : 1220 - 1227
[8] Study toward the total synthesis of the myrmicarin alkaloids.
Angle, SR
Kim, M
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U211 - U211
[9] Novel concise total synthesis of the quinazoline alkaloids.
Liu, JF
Ye, P
Kaselj, M
Sprague, K
Sargent, K
Isome, Y
Zhang, BL
Bi, G
Yohannes, D
Yu, LB
Baldino, CM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U391 - U391
[10] A straightforward access to pyrrolidine-based ligands for asymmetric synthesis
Delaye, Pierre-Olivier
Ahari, M'hamed
Vasse, Jean-Luc
Szymoniak, Jan
TETRAHEDRON-ASYMMETRY, 2010, 21 (20) : 2505 - 2511

← 1 2 3 4 5 →