A concise route to structurally diverse DMP 323 analogues via highly functionalized 1,4-diamines

被引：29

作者：

McReynolds, MD ^{[1
]}

Sprott, KT ^{[1
]}

Hanson, PR ^{[1
]}

机构：

[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 26期

关键词：

D O I：

10.1021/ol027074v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The utility of functionalized 1,4-diamines, produced via a temporary phosphorus tether (P-tether)/ring-closing metathesis (RCM)/hydrolysis sequence, is demonstrated in the synthesis of structurally diverse DMP 323 analogues. These 1,4-diamines are transformed into various seven-membered heterocycles via insertion of the appropriate nuclei "X". Subsequent derivatization generates heterocyclic diols that are similar in structure to DMP 323, a notable member of a class of highly potent inhibitors of HIV protease.

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页码：4673 / 4676

页数：4

相关论文

共 45 条

[1]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[2] AN UNAMBIGUOUS SYNTHESIS OF PYRAZOLES BY SULFUR EXTRUSION FROM 1,2,6-THIADIAZINES [J].

BARLUENGA, J ;

LOPEZORTIZ, JF ;

TOMAS, M ;

GOTOR, V .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (07) :1891-1895

[3] Temporary in situ aluminum and zinc tethering in Diels-Alder reactions [J].

Bertozzi, F ;

Olsson, R ;

Frejd, T .

ORGANIC LETTERS, 2000, 2 (09) :1283-1286

[4] Copper(I)-catalyzed intramolecular photocycloadditions of dicyclopentadiene derivatives linked by removable tethers [J].

Chebolu, R ;

Zhang, W ;

Galoppini, E ;

Gilardi, R .

TETRAHEDRON LETTERS, 2000, 41 (16) :2831-2834

[5]

Confalone PN, 1999, PROCESS CHEMISTRY IN THE PHARMACEUTICAL INDUSTRY, P201

[6] Synthesis of crossed [2+2] photocycloadducts: A novel approach to the synthesis of bridged bicyclic alkenes [J].

Crimmins, MT ;

Hauser, EB .

ORGANIC LETTERS, 2000, 2 (03) :281-284

[7]

De Lucca George V., 1998, Drugs of the Future, V23, P987, DOI 10.1358/dof.1998.023.09.473829

[8] 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

[9] Nonsymmetric P2/P2′ cyclic urea HIV protease inhibitors.: Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues [J].

De Lucca, GV ;

Kim, UT ;

Liang, J ;

Cordova, B ;

Klabe, RM ;

Garber, S ;

Bacheler, LT ;

Lam, GN ;

Wright, MR ;

Logue, KA ;

Erickson-Viitanen, S ;

Ko, SS ;

Trainor, GL .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (13) :2411-2423

[10] Ring-closing metathesis strategies to cyclic sulfamide peptidomimetics [J].

Dougherty, JM ;

Probst, DA ;

Robinson, RE ;

Moore, JD ;

Klein, TA ;

Snelgrove, KA ;

Hanson, PR .

TETRAHEDRON, 2000, 56 (50) :9781-9790

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