Studies on the stability of 1,7,9-trioxadispiro[5.1.5.2]pentadecane system: The common tricyclic acetal moiety in pinnatoxins

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 re...

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Bibliographic Details
Published inSynlett no. 6; pp. 603 - 607
Main Authors Ishihara, J, Sugimoto, T, Murai, A
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.06.1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
trioxadispiro[5.1.5.2]pentadecane
CIS-1,7,9-TRIOXADISPIRO<5.1.5.3>HEXADECANE
pinnatoxin
BIVALVE PINNA-MURICATA
SHELLFISH
dispiroacetal
BIS-SPIROACETAL
TRANS-1,7,9-TRIOXADISPIRO<5.1.5.3>HEXADECANE
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Summary: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.
ISSN:0936-5214
DOI:10.1055/s-1998-1742