Anodic oxidation reactions: the total synthesis of (+)-nemorensic acid

被引:14
作者
Liu, B [1 ]
Moeller, KD [1 ]
机构
[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(01)01506-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The anodic coupling of an enol ether to an oxygen nucleophile has been used as a key step in the total synthesis of (+)-nemorensic acid. The anodic cyclization reaction allows for a reversal in the way the tetrahydrofuran ring of the natural product is normally assembled and thus enables construction of the ring in a highly stereoselective fashion. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7163 / 7165
页数:3
相关论文
共 9 条
[1]   SYNTHESES WITH SULFONES .49. STEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (S)-(-)-3,9-DIMETHYL 6-(1-METHYLETHYL) (E)-5,8-DECADIEN-1-OL ACETATE, SEXUAL PHEROMONE OF YELLOW SCALE [J].
ALVAREZ, E ;
CUVIGNY, T ;
DUPENHOAT, CH ;
JULIA, M .
TETRAHEDRON, 1988, 44 (01) :119-126
[2]   Anodic electrochemistry and the use of a 6-volt lantern battery: A simple method for attempting electrochemically based synthetic transformations [J].
Frey, DA ;
Wu, N ;
Moeller, KD .
TETRAHEDRON LETTERS, 1996, 37 (46) :8317-8320
[3]   Enantiospecific synthesis of (+)-nemorensic acid, a necic acid component of the macropyrrolizidine alkaloid, nemorensine [J].
Honda, T ;
Ishikawa, F .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5542-5546
[4]   CHIRAL SYNTHESIS VIA ORGANOBORANES .5. ASYMMETRIC ALLYLBORATION VIA CHIRAL ALLYLDIALKYLBORANES - SYNTHESIS OF HOMOALLYLIC ALCOHOLS WITH EXCEPTIONALLY HIGH ENANTIOMERIC EXCESS [J].
JADHAV, PK ;
BHAT, KS ;
PERUMAL, PT ;
BROWN, HC .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :432-439
[5]   PYRROLIZIDINE ALKALOIDS .20. NEMORENSINE, AN ALKALOID FROM SENECIO-NEMORENSIS L [J].
KLASEK, A ;
SEDMERA, P ;
BOEVA, A ;
SANTAVY, F .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1973, 38 (08) :2504-2512
[6]   TOTAL SYNTHESIS OF (+/-)-NEMORENSIC ACID [J].
KLEIN, LL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2573-2574
[7]   Synthetic applications of anodic electrochemistry [J].
Moeller, KD .
TETRAHEDRON, 2000, 56 (49) :9527-9554
[8]   Anodic cyclization reactions: Reversing the polarity of ketene dithioacetal groups [J].
Sun, YM ;
Liu, B ;
Kao, J ;
d'Avignon, DA ;
Moeller, KD .
ORGANIC LETTERS, 2001, 3 (11) :1729-1732
[9]   Reversing the polarity of enol ethers: An anodic route to tetrahydrofuran and tetrahydropyran rings [J].
Sutterer, A ;
Moeller, KD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) :5636-5637