Diastereoselective synthesis of a novel lactam peptidomimetic exploiting vinylogous Mannich addition of 2-silyloxyfuran reagents

被引：31

作者：

Battistini, L

Rassu, G

Pinna, L

Zanardi, F

Casiraghi, G

机构：

[1] Univ Parma, Dipartimento Farmaceut, I-43100 Parma, Italy

[2] CNR, Ist Applicaz Tecn Chim Avanzate Problemi Agrobiol, I-07100 Sassari, Italy

[3] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(99)00051-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The total synthesis of a potential inhibitor of HIV-protease-the chiral nonracemic six-membered hydroxy lactam 6-has been accomplished, that involves, as key reaction, the highly diastereoselective vinylogous Mannich addition of furan-based silyloxy diene 7 to glyceraldeyde imine 8. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：765 / 773

页数：9

相关论文

共 21 条

[1]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[2]

2-E

[3] REACTIONS OF KETENE SILYL ACETALS WITH IMINE-COMPLEXES OF TITANIUM TETRACHLORIDE - NEW AND CONVENIENT ROUTES TO 5,6-DIHYDRO-2-PYRIDONES AND 5-AMINO-2-ALKENOATES [J].

BRANDSTADTER, SM ;

OJIMA, I .

TETRAHEDRON LETTERS, 1987, 28 (06) :613-616

[4]

Casiraghi G, 1998, ADV ASYMMETR SYNTH, V3, P113

[5] FURAN-BASED, PYRROLE-BASED, AND THIOPHENE-BASED SILOXYDIENES FOR SYNTHESES OF DENSELY FUNCTIONALIZED HOMOCHIRAL COMPOUNDS [J].

CASIRAGHI, G ;

RASSU, G .

SYNTHESIS-STUTTGART, 1995, (06) :607-626

[6] Stereospecific, stereoselective rearrangement of hexahydro-1,3-diazepin-2-ones to tetrahydropyrimidin-2-ones and imidazolidin-2-ones, a useful route for the synthesis of HIV protease inhibitors [J].

De Lucca, GV .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (14) :4755-4766

[7] Synthesis and evaluation of delta lactams as nonpeptide HIV-protease inhibitors [J].

DeLucca, GV .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (05) :501-504

[8] Design, synthesis, and evaluation of tetrahydropyrimidinones as an example of a general approach to nonpeptide HIV protease inhibitors [J].

DeLucca, GV ;

Liang, J ;

Aldrich, PE ;

Calabrese, J ;

Cordova, B ;

Klabe, RM ;

Rayner, MM ;

Chang, CH .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (11) :1707-1719

[9] Cyclic HIV protease inhibitors: Synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas [J].

Lam, PYS ;

Ru, Y ;

Jadhav, PK ;

Aldrich, PE ;

DeLucca, GV ;

Eyermann, CJ ;

Chang, CH ;

Emmett, G ;

Holler, ER ;

Daneker, WF ;

Li, LZ ;

Confalone, PN ;

McHugh, RJ ;

Han, Q ;

Li, RH ;

Markwalder, JA ;

Seitz, SP ;

Sharpe, TR ;

Bacheler, LT ;

Rayner, MM ;

Klabe, RM ;

Shum, LY ;

Winslow, DL ;

Kornhauser, DM ;

Jackson, DA ;

EricksonViitanen, S ;

Hodge, CN .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (18) :3514-3525

[10] RATIONAL DESIGN OF POTENT, BIOAVAILABLE, NONPEPTIDE CYCLIC UREAS AS HIV PROTEASE INHIBITORS [J].

LAM, PYS ;

JADHAV, PK ;

EYERMANN, CJ ;

HODGE, CN ;

RU, Y ;

BACHELER, LT ;

MEEK, JL ;

OTTO, MJ ;

RAYNER, MM ;

WONG, YN ;

CHANG, CH ;

WEBER, PC ;

JACKSON, DA ;

SHARPE, TR ;

ERICKSONVIITANEN, S .

SCIENCE, 1994, 263 (5145) :380-384