222847-80-5Relevant academic research and scientific papers
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.
Total synthesis of (+)-pramanicin and stereochemical elucidation of the natural product
Barrett, Anthony G. M.,Head, John,Smith, Marie L.,Stock, Nicholas S.
, p. 133 - 134 (2007/10/03)
Total synthesis of(+)-pramanicin is achieved through a 'one pot' Michael addition of an aminosilyl zincate species to an α,β-unsaturated lactam and quenching of the resultant enolate with an α,β-unsaturated γ,δ-epoxy aldehyde.
