Tetrahedron

Trienediolates of hexadienoic acids in synthesis. synthesis of retinoic and nor-retinoic acids.

MJ Aurell, I Carne, JE Clar, S Gil, R Mestres, M Parra…

Index: Aurell, Maria J.; Carne, Ismael; Clar, Jose E.; Gil, Salvador; Mestres, Ramon; Parra, Margarita; Tortajada, Amparo Tetrahedron, 1993 , vol. 49, # 27 p. 6089 - 6100

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Citation Number: 14

Abstract

Double deprotonation of either (E, E)-3-methyl-2, 4-hexadienoic acid 2, or 4, 6- dimethyldihydro-2-pyrone 3 generates apparently the same lithium trienediolate, which affords ω-hydroxy acids 9 on reaction with ketones 7. Hydroxy acids 9 are easily dehydrated to octatrienoic acids 5, which are structurally related to retinoic acid. Similarly, sorbic acid 1 leads to nor-retinoic acid analogs 6.