Ugi and Passerini Reactions of Biocatalytically Derived Chiral Aldehydes: Application to the Synthesis of Bicyclic Pyrrolidines and of Antiviral Agent Telaprevir

被引：56

作者：

Moni, Lisa ^{[1
]}

Banfi, Luca ^{[1
]}

Basso, Andrea ^{[1
]}

Carcone, Luca ^{[2
]}

Rasparini, Marcello ^{[2
]}

Riva, Renata ^{[1
]}

机构：

[1] Univ Genoa, Dept Chem & Ind Chem, I-16146 Genoa, Italy

[2] Chemessentia Srl, I-28100 Novara, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 07期

关键词：

HEPATITIS-C VIRUS; MULTICOMPONENT REACTION; PROTEASE INHIBITOR; ORGANIC-SYNTHESIS; MESO-DIOLS; ACID; HYDROLYSIS; DIVERSITY; CHEMISTRY; STRATEGY;

D O I：

10.1021/jo502829j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lipase mediated desymmetrization of a meso-diol (1,2-cyclopentanedimethanol) allows the synthesis of both enantiomers of some chiral aldehydes, whose behavior in Passerini and Ugi reactions has been explored. Exploiting these two complementary multicomponent reactions and coupling them with a subsequent cyclization process, we observed that 6 out of all 8 possible stereoisomers of peptidomimetic pyrrolidines can be obtained in good yields. The potential of these protocols has been proved by the development of a new efficient synthesis of antiviral drug telaprevir.

引用

页码：3411 / 3428

页数：18

共 52 条

[1] ENZYMATIC ESTER HYDROLYSIS AND SYNTHESIS - 2 APPROACHES TO CYCLOALKANE DERIVATIVES OF HIGH ENANTIOMERIC PURITY [J].

ADER, U ;

BREITGOFF, D ;

KLEIN, P ;

LAUMEN, KE ;

SCHNEIDER, MP .

TETRAHEDRON LETTERS, 1989, 30 (14) :1793-1796

[2] What do we know about multicomponent reactions? Mechanisms and trends for the Biginelli, Hantzsch, Mannich, Passerini and Ugi MCRs [J].

Alvim, Haline G. O. ;

da Silva Junior, Eufranio N. ;

Neto, Brenno A. D. .

RSC ADVANCES, 2014, 4 (97) :54282-54299

[3] ON THE OPTIMIZATION OF PIG PANCREATIC LIPASE-CATALYZED MONOACETYLATION OF PROCHIRAL DIOLS [J].

BANFI, L ;

GUANTI, G ;

RIVA, R .

TETRAHEDRON-ASYMMETRY, 1995, 6 (06) :1345-1356

[4] Passerini multicomponent reaction of protected α-aminoaldehydes as a tool for combinatorial synthesis of enzyme inhibitors [J].

Banfi, L ;

Guanti, G ;

Riva, R .

CHEMICAL COMMUNICATIONS, 2000, (11) :985-986

[5] Polyfunctionalized pyrrolidines by Ugi multicomponent reaction followed by palladium-mediated SN2′ cyclizations [J].

Banfi, Luca ;

Basso, Andrea ;

Cerulli, Valentina ;

Guanti, Giuseppe ;

Riva, Renata .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (04) :1608-1611

[6] Ugi multicomponent reaction followed by an intramolecular nucleophilic substitution: Convergent multicomponent synthesis of 1-sulfonyl 1,4-diazepan-5-ones and of their benzo-fused derivatives [J].

Banfi, Luca ;

Basso, Andrea ;

Guanti, Giuseppe ;

Kielland, Nicola ;

Repetto, Claudio ;

Riva, Renata .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06) :2151-2160

[7] The Alternative Route to Enantiopure Multicomponent Reaction Products: Biocatalytic or Organocatalytic Enantioselective Production of Inputs for Multicomponent Reactions [J].

Banfi, Luca ;

Basso, Andrea ;

Moni, Lisa ;

Riva, Renata .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (10) :2005-2015

[8] Long-Range Diastereoselectivity in an Ugi Reaction: Stereocontrolled and Diversity-Oriented Synthesis of Tetrahydrobenzoxazepines [J].

Banfi, Luca ;

Bagno, Alessandro ;

Basso, Andrea ;

De Santis, Carlo ;

Riva, Renata ;

Rastrelli, Federico .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (23) :5064-5075

[9] Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes [J].

Banfi, Luca ;

Riva, Renata ;

Basso, Andrea .

SYNLETT, 2010, (01) :23-41

[10]

Bomscheuer U. T., 2006, HYDROLASES ORGANIC S

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