Remote control of Diels-Alder additions. Enantioselective synthesis of (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural

被引：10

作者：

TheurillatMoritz, V ^{[1
]}

Guidi, A ^{[1
]}

Vogel, P ^{[1
]}

机构：

[1] UNIV LAUSANNE,CHIM SECT,BCH,CH-1015 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 20期

关键词：

D O I：

10.1016/S0957-4166(97)00433-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantiomerically pure (1S,4R,4'S,5'S)-1-(4',5'-dimethyl-dioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1 derived from the acetal of furfural and (2S,3S)-butane-2,3-diol underwent addition to 1-acetylvinyl para-nitrobenzoate in the presence of an excess of t-BuMe2SiOSO2CF3 to yield an 83:17 mixture of two diastereomeric products which was converted into (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone. (C) 1997 Elsevier Science Ltd.

引用

页码：3497 / 3501

页数：5

共 20 条

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TETRAHEDRON-ASYMMETRY, 2001, 12 (22) : 3155 - 3161
[2] ENANTIOSELECTIVE SYNTHESIS OF (R)-(-)-2-ACETYL-2,5,12-TRIHYDRO-1,2,3,4-TETRAHYDRO-6,11-NAPHTHACENEQUINONE VIA DIASTEREOSELECTIVE DIELS-ALDER CYCLOADDITION
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TETRAHEDRON LETTERS, 1993, 34 (06) : 1013 - 1016
[3] REMOTE SUBSTITUENT EFFECT ON THE ELECTROPHILIC ADDITIONS OF 1,3-DIENES - SYNTHESIS OF (2R)-5-(ACETOXYMETHYL)-2-ACETYL-1,2,3,4-TETRAHYDRO-10-METHOXYNAPHTHACENE-2,12-DIYL DIACETATE
MOSIMANN, H
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TETRAHEDRON, 1995, 51 (23) : 6495 - 6510
[4] THE DIELS-ALDER ADDUCT OF AN ENANTIOPURE 2-SULFINYLDIENE AND MALEIMIDE - (1S,2R,3S,SR)-3-METHYL-5-P-TOLUENESULFINYLCYCLOHEX-4-EN-1,2-DICARBOXIMIDE
GOSSELIN, P
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ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 : 94 - 96
[5] Synthesis of 1-(2-Methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-ones from Anilines and N-Vinyl Pyrrolidin-2-one Through Imino Diels-Alder Reaction Using 4-Nitro Phthalic Acid as Catalyst
Srinivasa, Aswathanarayana
Mahadevan, Kittappa M.
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SYNTHETIC COMMUNICATIONS, 2009, 39 (01) : 93 - 101
[6] The practical synthesis of a uterine relaxant, bis(2-{[(2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)-phenyl]ethyl}amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246)
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CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (08) : 1018 - 1023
[7] (R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid as a new chiral auxiliary for solid phase asymmetric Diels-Alder reactions
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TETRAHEDRON-ASYMMETRY, 2004, 15 (16) : 2515 - 2525
[8] (5R/5S)-2,5-Diphenyl-7-[trans- (1R/1S,2S/2R)-2-phenylcyclo hexyloxy]-2, 3,5,8-tetrahydro-1H-1,2,4-triazolo[ 1,2-a]pyridazine-1, 3-dione-water (1/1): A face-selective Diels-Alder reaction of 2-alkoxy-1,3-butadiene
Universidad de Oviedo, Oviedo, Spain
Acta Crystallogr Sect C Cryst Struct Commun, pt 12 (1941-1943):
[9] THE ASYMMETRIC DIELS-ALDER CYCLO-ADDITION USING ETHYL (-)-(Z)-(R)S-2-METHYL-3-(PARA-TOLYLSULFINYL)PROPENOATE - APPLICATION TO AN ENANTIOSELECTIVE SYNTHESIS OF (+)-EPI-BETA-SANTALENE
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