885674-86-2Relevant academic research and scientific papers
Stereoselective synthesis of 1,3-anti diols by an Ipc-mediated domino aldol-coupling/reduction sequence
Dieckmann, Michael,Menche, Dirk
, p. 228 - 231 (2013/03/28)
A novel domino process for 1,3-anti diol synthesis by the union of a methyl ketone with an aldehyde is described. The operationally simple procedure is based on an Ipc-boron-aldol coupling and subsequent Ipc-mediated reduction of the intermediate β-hydrox
Studies on C18-C20 aldol couplings of rhizopodin
Dieckmann, Michael,Rudolph, Sven,Lang, Carolin,Ahlbrecht, Wiebke,Menche, Dirk
, p. 2305 - 2315 (2013/09/02)
The aldol addition of an enol(ate) to a carbonyl compound is one of the most powerful and versatile C-C bond forming reactions. In complex target synthesis the coupling of two chiral partners may complicate the stereochemical outcome by multiple stereoinductions. Here, we report studies on pivotal aldol couplings employed in the rhizopodin synthesis, detailing the various directing effects exerted by the stereogenic centers present in this sterically hindered connection. Georg Thieme Verlag Stuttgart. New York.
Concise synthesis of the macrocyclic core of rhizopodin by a heck macrocyclization strategy
Dieckmann, Michael,Rudolph, Sven,Dreisigacker, Sandra,Menche, Dirk
supporting information, p. 10782 - 10788 (2013/02/23)
A highly convergent synthesis of the central dimeric core of the potent antibiotic macrolide rhizopodin is reported. Notable features of the highly concise route include an effective preparation of the key C8-C22 building block based on an iridium-catalyzed Krische allylation and a chemoselective cross-coupling approach toward the macrocycle involving a highly advantageous Heck reaction for macrocyclization.
Synthesis of a tetradehydro-disorazole C1
Niess, Barbara,Hartung, Ingo V.,Haustedt, Lars O.,Hoffmann, H. Martin R.
, p. 1132 - 1143 (2007/10/03)
The synthesis of a protected 9,9′,10,10′-tetradehydro- disorazole C1 is described. A C1-C8 oxazole fragment with an E-vinylic iodide terminus is coupled to a suitable C9-C19 enyne. The resulting ω-hydroxycarboxylic acid is cyclodimerized stepwi
Bryostatins: The asymmetric synthesis of the C1-C9 and C17-C27 fragments
De Brabander,Vandewalle
, p. 855 - 865 (2007/10/02)
The construction of the fragments C1-C9 3 and C17-C27 4a of the bryostatins in an enantioselective and highly diastereoselective fashion is described. The usefulness of the 'chiron' approach is illustrated with
Bryostatins: The asymmetric synthesis of C1-C9 and C11-C16 fragments
De Brabander,Vanhessche,Vandewalle
, p. 2821 - 2824 (2007/10/02)
The fragments C1-C9 19 and C11-C16 26 of the bryostatins are constructed in an enantioselective and highly diastereoselective fashion from respectively D-pantolactone (2) and L-erythrulose (3) as chiral template
