cis-2 Vitamin A acid and the hitherto unknown cis-2,cis-4 vitamin A acid are obtained by condensation of 3-methyl-5-(1,3,3-trimethylcyclohexenyl)penta-trans-2,trans-4-dienylidenephosphorane (IV) with cis-β-formyl-crotonic acid (II). Controlled stereomutation of the cis-2,cis-4-acid yielded cis-2- and all-trans vitamin A acid. cis-β-Formylcrotonic acid is isomerised to the trans-acid (I) by treatment with base.
C. F. Garbers, D. F. Schneider and J. P. van der Merwe, J. Chem. Soc. C, 1968, 1982 DOI: 10.1039/J39680001982
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