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Synlett 1998; 1998(6): 603-606
DOI: 10.1055/s-1998-1742
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Studies on the Stability of 1,7,9-Trioxadispiro[5.1.5.2]pentadecane System: The Common Tricyclic Acetal Moiety in Pinnatoxins

Jun Ishihara* , Tetsuya Sugimoto, Akio Murai
  • *Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, 060-0810, Japan; Fax + 011-706-2714; E-mail: amurai@sci.hokudai.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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The stability of the common dispiroacetal moiety in pinnatoxins, the 1,7,9-trioxadispiro[5.1.5.2]pentadecane system, was investigated. The tricyclic keto acetal, of the natural form, was most favored among the possible isomers, however, its methylated form was not so preferential to be isomerized readily in the presence of acid. These stability results were supported by MM2 and AM1.

pinnatoxin - dispiroacetal - trioxadispiro[5.1.5.2]pentadecane

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