Synthesis of 3,5,7-trioxapentacyclo[7.2.1.0(2,8).0(4,11).0(6,10)]dodecane. A novel diacetal trioxa-cage

被引:17
作者
Tsai, SH
Wu, HJ
Chung, WS
机构
[1] Department of Applied Chemistry, National Chiao Tung University, Hsinchu
关键词
unsubstituted diacetal trioxa-cage;
D O I
10.1002/jccs.199600064
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
3,5,7-Trioxapentacyclo[7.2.1.0(2,8).0(4,11).0(6,10)] dodecane, the parent compound of novel diacetal trioxa-cages, was synthesized from maleic anhydride cyclopentadiene adduct 1 by a four-step sequence. Attempts for the synthesis of monoaza dioxa-cage 12 failed. Ozonolysis of compound 9 in CH2Cl2-EtOH (1:1) at -78 degrees C followed by reduction with Me(2)S gave 13 in 65% yield.
引用
收藏
页码:445 / 449
页数:5
相关论文
共 10 条
[1]  
HOLMES HL, 1948, ORG REACTIONS, V4, P60
[2]  
Lin CC, 1996, SYNTHESIS-STUTTGART, P715
[3]   The first exclusive regioselective fragmentation of primary ozonides controlled by remote carbonyl groups [J].
Lin, CC ;
Wu, HJ .
TETRAHEDRON LETTERS, 1995, 36 (51) :9353-9356
[4]   FORMATION OF TETRAACETAL OXA-CAGES AND CONVEX OXA-CAGES ON OZONOLYSIS OF BICYCLO[2.2.2]OCTENES [J].
LIN, CC ;
WU, HJ .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1995, 42 (05) :815-820
[5]   Synthesis of novel tetraacetal oxa-cage compounds from 2-methylthiofurans [J].
Lin, CC ;
Huang, FJ ;
Lin, JC ;
Wu, HJ .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1996, 43 (02) :177-186
[6]   Synthesis of tetraacetal tetraoxa-cage compounds with alkyl substituents at different sites of the oxa-cage skeleton [J].
Lin, RL ;
Wu, CY ;
Chern, JH ;
Wu, HJ .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1996, 43 (03) :289-295
[7]   Synthesis of novel triacetal trioxa-cage compounds by ozonolysis of bicyclo[2.2.1]heptenes and bicyclo[2.2.2]octenes [J].
Wu, CY ;
Lin, CC ;
Lai, MC ;
Wu, HJ .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1996, 43 (02) :187-194
[8]   First exclusive regioselective fragmentation of primary ozonides controlled by remote carbonyl groups and a new method for determining the regiochemistry of carbonyl oxide formation [J].
Wu, HJ ;
Lin, CC .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3820-3828
[9]   NOVEL OXA-CAGE COMPOUNDS - SYNTHESIS, STRUCTURES, AND THE FORMATION MECHANISM OF TETRAACETAL OXA-CAGES AND CONVEX TETRAQUINANE OXA-CAGES [J].
WU, HJ ;
LIN, CC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7558-7566
[10]   NOVEL HETEROCYCLIC CAGE COMPOUNDS FROM 2-METHYLTHIOFURANS [J].
WU, HJ ;
HUANG, FJ ;
LIN, CC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (11) :770-771