Straightforward stereoselective synthesis of polyfunctionalized cyclohexenols using a multicomponent approach

被引:11
作者
Basso, Andrea [1 ]
Banfi, Luca [1 ]
Guanti, Giuseppe [1 ]
Riva, Renata [1 ]
机构
[1] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy
关键词
Cyclohexenols; Multicomponent reactions; Norbornenyl amino acids; Ring-opening reactions; Enantioselective synthesis; Diversity oriented synthesis; AMINO ACID-DERIVATIVES; UGI REACTION; ASYMMETRIC-SYNTHESIS; OXABICYCLIC ALKENES; DRUG DISCOVERY; METATHESIS;
D O I
10.1016/j.tet.2010.01.097
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An intramolecular Ugi 5-centre-4-component reaction (U-5C-4CR) followed by a palladium-catalysed ring-opening has been employed to transform oxabicycloheptene-based beta-amino acids into two families of regioisomeric polyfunctionalised cyclohexenols. The whole process is completely stereoselective and enantiomerically pure products are obtained in high overall yields. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2390 / 2397
页数:8
相关论文
共 17 条
[1]   Isocyanide-based multicomponent reactions in drug discovery [J].
Akritopoulou-Zanze, Irini .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2008, 12 (03) :324-331
[2]   Recent advances in the development and applications of post-Ugi transformations [J].
Akritopoulou-Zanze, Irini ;
Djuric, Stevan W. .
HETEROCYCLES, 2007, 73 (01) :125-+
[3]   REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF SUBSTITUTED CYCLOHEXENEDIOLS FROM 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-OLS AND ORGANO-LITHIUM REAGENTS [J].
ARJONA, O ;
DELAPRADILLA, RF ;
GARCIA, E ;
MARTINDOMENECH, A ;
PLUMET, J .
TETRAHEDRON LETTERS, 1989, 30 (46) :6437-6440
[4]   A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent Ugi reaction [J].
Basso, A ;
Banfi, L ;
Riva, R ;
Guanti, G .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :575-579
[5]   U-4C-3CR versus U-5C-4CR and stereochemical outcomes using suitable bicyclic β-amino acid derivatives as bifunctional components in the Ugi reaction [J].
Basso, A ;
Banfi, L ;
Riva, R ;
Guanti, G .
TETRAHEDRON LETTERS, 2004, 45 (03) :587-590
[6]   Preparation of optically pure fused polycyclic scaffolds by Ugi reaction followed by olefin and enyne metathesis [J].
Basso, Andrea ;
Banfi, Luca ;
Riva, Renata ;
Guanti, Giuseppe .
TETRAHEDRON, 2006, 62 (37) :8830-8837
[7]   Asymmetric synthesis of the putative structure of (-)-oryzoxymycin [J].
Bunnage, ME ;
Ganesh, T ;
Masesane, IB ;
Orton, D ;
Steel, PG .
ORGANIC LETTERS, 2003, 5 (03) :239-242
[8]   A planning strategy for diversity-oriented synthesis [J].
Burke, MD ;
Schreiber, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :46-58
[9]   Identification of Lead Compounds As Antagonists of Protein Bcl-xL with a Diversity-Oriented Multidisciplinary Approach [J].
Di Micco, Simone ;
Vitale, Romina ;
Pellecchia, Maurizio ;
Rega, Michele F. ;
Riva, Renata ;
Basso, Andrea ;
Bifulco, Giuseppe .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (23) :7856-7867
[10]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89