Diastereoselective Synthesis of a Spironoraristeromycin Using an Acylnitroso Diels-Alder Reaction

被引：17

作者：

Lin, Weimin ^{[1
]}

Virga, Kristopher G. ^{[1
]}

Kim, Kyung-Hee ^{[1
]}

Zajicek, Jaroslav ^{[1
]}

Mendel, David ^{[2
]}

Miller, Marvin J. ^{[1
]}

机构：

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

[2] Eli Lilly & Co, Lilly Corp Ctr, Indianapolis, IN 46285 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 16期

关键词：

S-ADENOSYLHOMOCYSTEINE HYDROLASE; CARBOCYCLIC NUCLEOSIDES; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; POTENT; CYCLIZATION; NEPLANOCIN; ANALOGS;

D O I：

10.1021/jo900877b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tert-butyl N-hydroxycarbamate-derived nitroso reagent I reacted with N-Cbz-protected spirocyclic diene 2 to provide spirocycloadduct 3. Here we describe the efficient conversion of 3 into the novel carbocyclic nucleoside spironoraristeromycin 4.

引用

页码：5941 / 5946

页数：6

共 54 条

[1]

Adamo MFA, 2008, TARG HETEROCYCL SYST, V11, P396

[2]

Agbaria R, 1997, ONCOL RES, V9, P111

[3] CONFORMATIONAL-ANALYSIS OF SUGAR RING IN NUCLEOSIDES AND NUCLEOTIDES - NEW DESCRIPTION USING CONCEPT OF PSEUDOROTATION [J].

ALTONA, C ;

SUNDARALINGAM, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (23) :8205-+

[4] 2′-Spiro ribo- and arabinonucleosides:: synthesis, molecular modelling and incorporation into oligodeoxynucleotides [J].

Babu, BR ;

Keinicke, L ;

Petersen, M ;

Nielsen, C ;

Wengel, J .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (20) :3514-3526

[5]

Banik B.K., 2005, ORG SYN, V81, P188

[6] An efficient one-pot synthesis of 6-alkoxy-8,9-dialkylpurines via reaction of 5-amino-4-chloro-6-alkylaminopyrimidines with N,N-dimethylalkaneamides and alkoxide ions [J].

Baraldi, PG ;

Broceta, AU ;

de las Infantas, MJP ;

Mochun, JJD ;

Espinosa, A ;

Romagnoli, R .

TETRAHEDRON, 2002, 58 (38) :7607-7611

[7] CHIROSPECIFIC SYNTHESIS OF (1S,3R)-1-AMINO-3-(HYDROXYMETHYL)CYCLOPENTANE, PRECURSOR FOR CARBOCYCLIC NUCLEOSIDE SYNTHESIS - DIECKMANN CYCLIZATION WITH AN ALPHA-AMINO-ACID [J].

BERGMEIER, SC ;

COBAS, AA ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2369-2376

[8] Reactions of nitroso hetero-diels-alder cycloadducts with azides: Stereoselective formation of triazolines and aziridines [J].

Bodnar, Brian S. ;

Miller, Marvin J. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (10) :3929-3932

[9] Total chemoenzymatic synthesis of (-)-3′-methylaristeromycin [J].

Bremond, Paul ;

Audran, Gerard ;

Aubin, Yoann ;

Monti, Honore .

SYNLETT, 2007, (07) :1124-1126

[10]

Casu F, 2007, CURR ORG CHEM, V11, P999

← 1 2 3 4 5 6 →