Simple syntheses of isomers of muconaldehyde and 2-methylmuconaldehyde

BT Golding, G Kennedy, WP Watson

Index: Golding, Bernard T.; Kennedy, Gordon; Watson, William P. Tetrahedron Letters, 1988 , vol. 29, # 46 p. 5991 - 5994

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Citation Number: 29

Abstract

Abstract Periodate oxidation of cis-1, 2-dihydrocatechol (3a) affords (Z, Z)-muconaldehyde (2b), which can be readily converted (thermolysis and triethylamine catalysis, respectively) into its (E, Z)-(2c) and (E, E)-isomer (2a). Similarly, cis-1, 2-dihydro-3-methylcatechol (3b) gives (Z, Z)-2-methylmuconaldehyde (2d) and thence (E, E)-2-methylmuconaldehyde (2c).