Total synthesis of aspidophytine

被引:36
作者
Marino, Joseph P. [1 ]
Cao, Ganfeng [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
基金
美国国家卫生研究院;
关键词
aspidophytine; haplophytine; aspidosperma alkaloids; quaternary carbon center; chiral vinyl sulfoxide; ketene-lactonization; Marino annulation reaction; enantiospecific; tandem;
D O I
10.1016/j.tetlet.2006.08.115
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A total synthesis of aspidophytine was accomplished by employing a newly developed strategy for the enantiospecific syntheses of aspidosperma alkaloids. The key steps involve a novel ketene-lactonization reaction of a chiral vinyl sulfoxide (Marino annulation reaction) to set up the chiral quaternary carbon center, and a tandem Michael addition-alkylation reaction sequence to form the polycyclic core structure. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7711 / 7713
页数:3
相关论文
共 17 条
[1]  
BORCH RF, 1968, TETRAHEDRON LETT, V17, P61
[2]  
COREY EJ, 1979, TETRAHEDRON LETT, V5, P399
[3]   PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].
ECHAVARREN, AM ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5478-5486
[4]   ASYMMETRIC-SYNTHESIS OF CHIRAL ORGANOSULFUR COMPOUNDS USING N-SULFINYLOXAZOLIDINONES [J].
EVANS, DA ;
FAUL, MM ;
COLOMBO, L ;
BISAHA, JJ ;
CLARDY, J ;
CHERRY, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :5977-5985
[5]  
GROBELNY D, 1979, TETRAHEDRON LETT, V28, P2639
[6]   Enantioselective total synthesis of aspidophytine [J].
He, F ;
Bo, YX ;
Altom, JD ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6771-6772
[7]  
KELLY TR, 1985, TETRAHEDRON, V41, P3033
[8]   STEREOSPECIFIC SYNTHESIS OF (R)-S-ADENOSYL-1,8-DIAMINO-3-THIOOCTANE AND (S)-S-ADENOSYL-1,8-DIAMINO-3-THIOOCTANE, A POTENT INHIBITOR OF POLYAMINE BIOSYNTHESIS - COMPARISON OF ASYMMETRIC INDUCTION VS ENANTIOMERIC SYNTHESIS [J].
LIU, C ;
COWARD, JK .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (07) :2094-2101
[9]   Total synthesis of (+)-aspidospermidine: A new strategy for the enantiospecific synthesis of aspidosperma alkaloids [J].
Marino, JP ;
Rubio, MB ;
Cao, GF ;
de Dios, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13398-13399
[10]   ENANTIOSPECIFIC LACTONIZATIONS OF CHIRAL 1-(ARYLSULFINYL)CYCLOHEXENES WITH CHLOROKETENES [J].
MARINO, JP ;
PEREZ, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (24) :7643-7644