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Synthesis 1996; 1996(6): 715-718
DOI: 10.1055/s-1996-4291
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Synthesis of Tetraacetal Pentaoxa-Cages and Convex Oxa-Cages by Ozonolysis of 7-Oxabicyclo[2.2.1]heptenes

Chu-Chung Lin, Hsien-Jen Wu*
  • *Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan, Republic of China, Fax +886(35)723764
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Publication Date:
31 December 2000 (online)

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Tetraacetal pentaoxa-cage compounds 4a and 4b and convex oxa-cage compounds 6, 7 and 8 are synthesized from alkylfurans in three steps. Ozonolysis of the endo adducts 2a and 2b in dichloromethane at -78°C followed by reduction with dimethyl sulfide gave the tetraacetal pentaoxa-cages 4a and 4b in 85-90% yields, respectively. Ozonolysis of 2a and 2b in dichloromethane at -78°C followed by treatment with triethylamine gave the convex oxa-cages 6, 7 and 8 in 85-90% yields, respectively. The synthesis of the tetraacetal pentaoxa-cage 12, possessing aromatic substituents directly on the skeleton of the oxa-cages, has also been accomplished.

tetraacetal-pentaoxa-cages - convex oxa-cages - ozonolysis - 7-oxabicyclo[2.2.1]heptenes

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