Synthesis of pentaoxa[5]peristylanes

Abstract

The synthesis of alkyl-substituted pentaoxa[5]peristylanes has been accomplished by ozonolysis of 2,3-bisendo-7-anti-triacylnorbornenes 6a-d and by direct chemical transformation of the tetraacetal tetraoxa cages 11 and 12. Various reaction conditions have been used to optimize the overall yield for the synthesis of methyl group substituted pentaoxa[5]peristylane 7d. Ozonolysis of 6d in CDCl3 at -78 degrees C without reduction was performed to study the ozonolysis chemistry of the triacylnorbornenes 6a-d. The synthesis of the parent (unsubstituted) compound 25 of pentaoxa[5]peristylane has been accomplished by a three-step efficient-sequence with a maximum 45% overall yield via ozonolysis of the dihemiacetal 24. The structure of pentaoxa[5]peristylanes was proven by X-ray analysis of the parent compound 25. The syntheses of the triacetal tetraoxa cage 26, a new type of oxa cage, and a new entry for the synthesis of the parent compound 33 of tetraacetal tetraoxa cages were also demonstrated.