67711-05-1Relevant articles and documents
Vinyltin acetals in terpenic and nor-terpenic synthesis
Launay, Valerie,Beaudet, Isabelle,Quintard, Jean-Paul
, p. 937 - 946 (2007/10/03)
Vinyltin acetals obtained by stannylmetallation of homopropargyl acetals with Bu3SnMgMe/CuCN (E configuration) or by titanation of the corresponding alkyltin acetals (Z configuration) have been proved to be efficient storable precursors for the stereoselective synthesis of terpenoids, under mild experimental conditions.Due to the presence of a nucleophilic centre (Csp2-Sn bond) and of a protected electrophilic centre, they are also useful intermediates for an iterative synthesis of retinal and nor-retinoids. - Keywords: vinyltin; acetal; vinyllithium; monoterpenoid; retinal; nor-retinoid
A new prenylation method using the lithium enolate of prenal. Reaction with polyunsaturated aldehydes. A short access to retinal
Duhamel, Lucette,Guillemont, Jerome,Poirier, Jean-Marie,Chabardes, Pierre
, p. 4499 - 4500 (2007/10/02)
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.
7-cis,9-cis,11-cis-retinal, all-cis-vitamin A, and 7-cis,9-cis,11-cis-12-fluororetinal. New geometric isomers of vitamin A and carotenoids. 12
Asato,Kini,Denny,Liu
, p. 2923 - 2924 (2007/10/02)
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