New enantioselective entry to cycloheptane amino acid polyols

被引：26
作者：
Curti, C
Zanardi, F
Battistini, L
Sartori, A
Rassu, G
Auzzas, L
Roggio, A
Pinna, L
Casiraghi, G
机构：
[1] Univ Parma, Dipartimento Farmaceut, I-43100 Parma, Italy
[2] CNR, Ist Chim Biomol, I-07040 Sassari, Italy
[3] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 01期
关键词：
D O I：
10.1021/jo0520137
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A diversity-oriented protocol has been developed for the assembly of densely hydroxylated cycloheptane amino acids via succession of a vinylogous Mukaiyama aldol reaction (VMAR), a Morita-Baylis-Hillman reaction (MBHR), and an intramolecular pinacol coupling reaction (IPCR). The plan utilizes Dor L-configured glyceraldehyde derivatives as "chiral" surrogates of glyoxal and N-[(tert-butoxycarbonyl)2-(tert-butyldimethylsilyl)oxy]pyrrole as the synthetic equivalent of the alpha,gamma-dianion of gamma-aminobutanoic acid. The parallel, asymmetric syntheses of four cycloheptane representatives proceed with high diastereocontrol and virtually complete enantioselectivity in ten steps and overall yields of 15-37%.
引用
收藏
页码：225 / 230
页数：6
相关论文
共 27 条
[1]   Synthesis and glycosidase inhibitory activity of new penta-substituted C8-glycomimetics [J].
Andriuzzi, O ;
Gravier-Pelletier, C ;
Vogel, P ;
Le Merrer, Y .
TETRAHEDRON, 2005, 61 (30) :7094-7104
[2]  
[Anonymous], ADV AMINO ACID MIMET
[3]   Specific alpha-galactosidase inhibitors, N-methylcalystegines - Structure/activity relationships of calystegines from Lycium chinense [J].
Asano, N ;
Kato, A ;
Miyauchi, M ;
Kizu, H ;
Tomimori, T ;
Matsui, K ;
Nash, RJ ;
Molyneux, RJ .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1997, 248 (02) :296-303
[4]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[5]   The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].
Casiraghi, G ;
Zanardi, F ;
Appendino, G ;
Rassu, G .
CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972
[6]  
Denmark SE, 2005, ANGEW CHEM INT EDIT, V44, P4682, DOI 10.1002/anie.200462338
[7]   Samarium(II)-iodide-mediated cyclizations in natural product synthesis [J].
Edmonds, DJ ;
Johnston, D ;
Procter, DJ .
CHEMICAL REVIEWS, 2004, 104 (07) :3371-3403
[8]   TROPANE DERIVATIVES FROM CALYSTEGIA-SEPIUM [J].
GOLDMANN, A ;
MILAT, ML ;
DUCROT, PH ;
LALLEMAND, JY ;
MAILLE, M ;
LEPINGLE, A ;
CHARPIN, I ;
TEPFER, D .
PHYTOCHEMISTRY, 1990, 29 (07) :2125-2127
[9]  
GOODMAN M, 2003, HOUBEN WEYL METHODS, V22, P693
[10]   Carbohydrate-based mimetics in drug design: Sugar amino acids and carbohydrate scaffolds [J].
Gruner, SAW ;
Locardi, E ;
Lohof, E ;
Kessler, H .
CHEMICAL REVIEWS, 2002, 102 (02) :491-514
123