Chemoenzymatic asymmetric total synthesis of phosphodiesterase inhibitors:: Preparation of a polycyclic pyrazolo[3,4-d]pyrimidine from an acylnitroso Diels-Alder cycloadduct-derived aminocyclopentenol

被引：34

作者：

Jiang, MXW ^{[1
]}

Warshakoon, NC ^{[1
]}

Miller, MJ ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 07期

关键词：

D O I：

10.1021/jo0484070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enzymatic resolution of Boc-protected 4-aminocyclopenten1-ol 4c gave both enantiomers 5c and 6c in high ee. Boc removal and separate condensation with chloropyrazolopyrimidine 18 provided elaborated 1,4-aminocyclopentenol derivatives 20 and 26, respectively. Separate treatment of 20 and 26 with Pd(0) under basic conditions induced cyclization to unsaturated polycycles 22 and 27, which, upon catalytic hydrogenation, were transformed to new cyclopentane-containing pyrazolopyrimidines 24 and 28, analogues of recently described novel phosphodiesterase inhibitors.

引用

页码：2824 / 2827

页数：4

共 37 条

[1] SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].

AGROFOGLIO, L ;

SUHAS, E ;

FARESE, A ;

CONDOM, R ;

CHALLAND, SR ;

EARL, RA ;

GUEDJ, R .

TETRAHEDRON, 1994, 50 (36) :10611-10670

[2] Potent tetracyclic guanine inhibitors of PDE1 and PDE5 cyclic guanosine monophosphate phosphodiesterases with oral antihypertensive activity [J].

Ahn, HS ;

Bercovici, A ;

Boykow, G ;

Bronnenkant, A ;

Chackalamannil, S ;

Chow, J ;

Cleven, R ;

Cook, J ;

Czarniecki, M ;

Domalski, C ;

Fawzi, A ;

Green, M ;

Gundes, A ;

Ho, G ;

Laudicina, M ;

Lindo, N ;

Ma, K ;

Manna, M ;

McKittrick, B ;

Mirzai, B ;

Nechuta, T ;

Neustadt, B ;

Puchalski, C ;

Pula, K ;

Silverman, L ;

Smith, E ;

Stamford, A ;

Tedesco, RP ;

Tsai, HG ;

Tulshian, D ;

Vaccaro, H ;

Watkins, RW ;

Weng, XY ;

Witkowski, JT ;

Xia, Y ;

Zhang, HT .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (14) :2196-2210

[3] CYCLIC-NUCLEOTIDE PHOSPHODIESTERASES - FUNCTIONAL IMPLICATIONS OF MULTIPLE ISOFORMS [J].

BEAVO, JA .

PHYSIOLOGICAL REVIEWS, 1995, 75 (04) :725-748

[4]

Bell A.S., 1993, European Patent, Patent No. [526004, 0526004]

[5] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].

Berecibar, A ;

Grandjean, C ;

Siriwardena, A .

CHEMICAL REVIEWS, 1999, 99 (03) :779-844

[6] SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].

BORTHWICK, AD ;

BIGGADIKE, K .

TETRAHEDRON, 1992, 48 (04) :571-623

[7] PREPARATION OF NUCLEOTIDE MIMICS WITH POTENT INHIBITORY ACTIVITY AGAINST HIV REVERSE-TRANSCRIPTASE [J].

COE, DM ;

ORR, DC ;

ROBERTS, SM ;

STORER, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :3378-3379

[8] SYNTHESIS OF SOME MIMICS OF NUCLEOSIDE TRIPHOSPHATES [J].

COE, DM ;

HILPERT, H ;

NOBLE, SA ;

PEEL, MR ;

ROBERTS, SM ;

STORER, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) :312-314

[9] New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides [J].

Crimmins, MT .

TETRAHEDRON, 1998, 54 (32) :9229-9272

[10] Inhibitors of types I and V phosphodiesterase: Elevation of cGMP as a therapeutic strategy [J].

Czarniecki, M ;

Ahn, HS ;

Sybertz, EJ .

ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 31, 1996, 31 :61-70

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