Synthesis of the sedum and related alkaloids: A personal perspective

被引:9
作者
Bates, Roderick W. [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
Alkaloids; Synthesis; Sedum; AZA-MICHAEL REACTION; ASYMMETRIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; PIPERIDINE ALKALOIDS; CONJUGATE ADDITION; ISOXAZOLIDINES; HYDROXYLAMINE; (-)-PINIDINOL; ALCOHOLS; NITROGEN;
D O I
10.1016/j.tetlet.2017.12.026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Significant recent contributions to the synthesis of the sedum alkaloids are discussed. Related compounds, such as pinidinol, porantheridine, dumetorine and the tetraponerines are also included. The syntheses are categorised according to the key motif or chemistry employed: isoxazolidines, metathesis, asymmetric aza-Michael, heterocycle lithiation, organocatalysis, aromatic heterocycles and chiral imines. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:559 / 567
页数:9
相关论文
共 46 条
[21]   Regioselective and Stereoselective Copper(I)-Promoted Allylation and Conjugate Addition of N-Boc-2-lithiopyrrolidine and N-Boc-2-lithiopiperidine [J].
Coldham, Iain ;
Leonori, Daniele .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12) :4069-4077
[22]   FeCl3•6H2O, a Catalyst for the Diastereoselective Synthesis of cis-Isoxazolidines from N-Protected δ-Hydroxylamino Allylic Acetates [J].
Cornil, Johan ;
Guerinot, Amandine ;
Reymond, Sebastien ;
Cossy, Janine .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) :10273-10287
[23]   Enantioselective allyltitanations and metathesis reactions. application to the synthesis of piperidine alkaloids (+)-sedamine and (-)-prosophylline [J].
Cossy, J ;
Willis, C ;
Bellosta, V ;
BouzBouz, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :1982-1992
[24]   Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition [J].
Davies, Stephen G. ;
Fletcher, Ai M. ;
Roberts, Paul M. ;
Smith, Andrew D. .
TETRAHEDRON, 2009, 65 (49) :10192-10213
[25]   N-sulfinyl β-amino Weinreb amides:: Synthesis of enantiopure β-amino carbonyl compounds.: Asymmetric synthesis of (+)-sedridine and (-)-allosedridine [J].
Davis, FA ;
Prasad, KR ;
Nolt, MB ;
Wu, YZ .
ORGANIC LETTERS, 2003, 5 (06) :925-927
[26]   Asymmetric Synthesis of Acyclic 1,3-Amino Alcohols by Reduction of N-Sulfinyl β-Amino Ketones. Formal Synthesis of (-)-Pinidinol and (+)-Epipinidinol [J].
Davis, Franklin A. ;
Gaspari, Paul M. ;
Nolt, Brad M. ;
Xu, Peng .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (24) :9619-9626
[27]   Palladium(0)-catalyzed cascade one-pot synthesis of isoxazolidines [J].
Dongol, KG ;
Tay, BY .
TETRAHEDRON LETTERS, 2006, 47 (06) :927-930
[28]   Enantioselective organocatalytic intramolecular aza-Michael reaction:: a concise synthesis of (+)-sedamine., (+)-allosedamine, and (+)-coniine [J].
Fustero, Santos ;
Jimenez, Diego ;
Moscardo, Javier ;
Catalan, Silvia ;
del Pozo, Carlos .
ORGANIC LETTERS, 2007, 9 (25) :5283-5286
[29]   N-Sulfinyl Amines as a Nitrogen Source in the Asymmetric Intramolecular Aza-Michael Reaction: Total Synthesis of (-)-Pinidinol [J].
Fustero, Santos ;
Monteagudo, Silvia ;
Sanchez-Rosello, Maria ;
Flores, Sonia ;
Barrio, Pablo ;
del Pozo, Carlos .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) :9835-9845
[30]   Enantioselective Iridium-Catalyzed Allylic Substitutions with Hydroxamic Acid Derivatives as N-Nucleophiles [J].
Gaertner, Martin ;
Jaekel, Mascha ;
Achatz, Manuel ;
Sonnenschein, Christoph ;
Tverskoy, Olena ;
Helmchen, Guenter .
ORGANIC LETTERS, 2011, 13 (11) :2810-2813