886986-52-3Relevant academic research and scientific papers
Synthesis of Strained 1,3-Diene Macrocycles via Copper-Mediated Castro-Stephens Coupling/Alkyne Reduction Tandem Reactions
Li, Wei,Schneider, Christopher M.,Georg, Gunda I.
supporting information, p. 3902 - 3905 (2015/08/18)
A copper-mediated macrocyclization involving the reaction of a vinyl iodide and a terminal alkyne followed by an in situ reduction of the enyne intermediate is reported. The reaction generates a conjugated Z-double bond within a strained medium-size lacto
Studies towards the synthesis of the northern polyene of viridenomycin and synthesis of Z-double bond analogues
Knowles, Jonathan P.,O'Connor, Victoria E.,Whiting, Andrew
, p. 1876 - 1886 (2011/04/25)
Viridenomycin is a structurally challenging, potentially biologically valuable molecule which has yet to succumb to total synthesis. Its instability, perhaps particularly associated with the northern polyene may contribute to the difficulties of piecing this molecule together. The synthesis of northern polyene models, including potentially stabilised analogues incorporating benzene rings as Z-alkene replacements, have been prepared using an efficient series of cross-coupling reactions. The resulting polyenes and polyene surrogates have been converted into tetraene ester and amide models of the viridenomycin system. These analogues have sufficient stability compared with the unsubstituted northern polyene analogue to be viable for future developing a strategy for the construction of viridenomycin and analogues.
Concise strategy to the core structure of the macrolide queenslandon
Khartulyari, Anton S.,Kapur, Manmohan,Maier, Martin E.
, p. 5833 - 5836 (2007/10/03)
(Diagram presented) The fully functionalized core structure of the macrolactone queenslandon was prepared using a novel strategy consisting of a glycolate aldol reaction and hydroboration of the derived enol ether 17 followed by Suzuki cross-coupling with an iodostyrene. After conversion of the cross-coupling product to the seco acid 22, Mitsunobu macrolactonization and protecting group manipulations led to the queenslandon model 5.
