123932-69-4Relevant academic research and scientific papers
Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol
Takada, Yuki,Caner, Joaquim,Kaliyamoorthy, Selvam,Naka, Hiroshi,Saito, Susumu
supporting information, p. 18025 - 18032 (2017/12/08)
We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(?)-carvone by avoiding otherwise necessary protection/deprotection steps.
Fleming-Tamao oxidation and masked hydroxyl functionality: Total synthesis of (+)-pramanicin and structural elucidation of the antifungal natural product (-)-pramanicin
Barrett, Anthony G. M.,Head, John,Smith, Marie L.,Stock, Nicholas S.,White,Williams
, p. 6005 - 6018 (2007/10/03)
The total synthesis of (+)-pramanicin (41b) is reported, thereby establishing the relative and absolute stereochemistry of the naturally occurring antifungal agent. The key steps involve (i) conjugate addition of the diethyl((diethylamino)diphenylsilyl)zincate to a suitably protected γ- lactam 3 and quenching of the resultant enolate with the α,β-unsaturated γ,δ-epoxy aldehyde 2 (X = H), (ii) Ni(acac)2-catalyzed hydroxylation of a β-dicarbonyl array, and (iii) Fleming-Tamao oxidation to reveal the masked C-3 hydroxyl group.
