Tetrahedron Letters p. 4499 - 4500 (1991)
Update date:2022-08-06
Topics: Organic synthesis Retinal Prenylation
Duhamel, Lucette
Guillemont, Jerome
Poirier, Jean-Marie
Chabardes, Pierre
The enolate of prenal 1 prepared from the corresponding silyl enol ether 2 or enol acetate 3 led to a γ-regiospecific reaction with polyunsaturated aldehydes 4 yielding dihydropyrans 5 leading after hydrolysis to polyenals 7. This process allows the introduction of the isoprenyl skeleton. A synthesis of retinal, from β-ionylidenacetaldehyde is reported.
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