Synthesis of optically active polycyclic compounds by Diels-Alder reactions of (+)-nopadiene

被引：2
|
作者：
Minuti, L
Taticchi, A
Marrocchi, A
Broggi, A
Gacs-Baitz, E
机构：
[1] Univ Studi Perugia, Dipartimento Chim, I-06123 Perugia, Italy
[2] Hungarian Acad Sci, Cent Inst Chem, H-1525 Budapest, Hungary
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 20期
关键词：
D O I：
10.1016/j.tetasy.2004.07.063
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
4-Oxo-2-cyclopentenylacetate 1 underwent a tandem Diels-Alder reaction with (+)-nopadiene 3 to lead to C-2-symmetric optically active polycyclic ketone 4. All attempts to carry out similar processes with acetoxy ketone 1 and two different dienes, that is, (+)-nopadiene 3 and isoprene 6 or 2,3-dimethyl-1,3-butadiene 7 were unsuccessful. Enantiomerically pure polycyclic ketones 8 and 9 were prepared by Diels-Alder cycloaddition between optically active alpha,beta-unsaturated ketone 5 and dienes 6 and 7. (C) 2004 Elsevier Ltd. All rights reserved.
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页码：3245 / 3248
页数：4
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