3043-64-9Relevant academic research and scientific papers
Total Synthesis of the Marine Macrolide Amphidinolide F
Ferrié, Laurent,Fenneteau, Johan,Figadère, Bruno
, p. 3192 - 3196 (2018/06/11)
A new and efficient convergent approach toward the synthesis of amphidinolide F is described through the assembly of three fragments. The two trans-tetrahydrofurans were built by a diastereoselective C-glycosylation with titanium enolate of bulky N-acetyloxazolidinethiones. The side chain was inserted by a Liebeskind-Srogl cross-coupling reaction. A sulfone condensation/desulfonylation sequence, a Stille cross-coupling, and a macrolactonization were applied to connect the fragments.
Modified Julia Olefination on Anhydrides: Extension and Limitations. Application to the Synthesis of Maculalactone B
Dussart, Nicolas,Trinh, Huu Vinh,Gueyrard, David
supporting information, p. 4790 - 4793 (2016/10/14)
The preparation of exo-enol esters from cyclic anhydrides is reported using a modified Julia olefination. The reaction is highly stereoselective. The Smiles rearrangement can be performed in a one-pot process, giving a straightforward access to exo-enol lactones. Furthermore, the reaction was extended to semistabilized sulfones, and this methodology was applied to the synthesis of maculalactone B.
A diels-alder approach to (-)-ovalicin
Tiefenbacher, Konrad,Arion, Vladimir B.,Mulzer, Johann
, p. 2690 - 2693 (2008/03/12)
A round at the Oval: The antiangiogenic activity of the natural product ovalicin has sparked significant interest. A highly efficient enantio- and diastereoselective total synthesis of ovalicin proved successful in which the key step involved an endo sele
Total synthesis of (-)-spirotryprostatin B: Synthesis and related studies
Marti, Christiane,Carreira, Erick M.
, p. 11505 - 11515 (2007/10/03)
The total synthesis of spirotryprostatin B, a cytostatic spiro[pyrrolidine-3,3′-oxindole] alkaloid, is described. The key step of the synthetic approach consists of the application of the Mgl 2-mediated ring-expansion reaction of a spiro[cyclopropane-1, 3′-oxindole] with an aldimine, leading to rapid assembly of the spirotryprostatin core. The route documents the installation of the prenyl side chain by Julia-Kocienski olefination of a key aldehyde precursor, a transformation that ultimately allows for facile synthesis of analogues and facilitates structure-activity relationships studies.
