183894-33-9Relevant academic research and scientific papers
Formal synthesis of dictyostatin and synthesis of two dictyostatin analogues
Gallon, Julien,Esteban, Jorge,Bouzbouz, Samir,Campbell, Matthew,Reymond, Sébastien,Cossy, Janine
supporting information, p. 11788 - 11797 (2012/11/07)
A formal convergent synthesis of dictyostatin from (R)-Roche ester is described. Synthetic highlights include a Ni-catalyzed Nozaki-Hiyama-Kishi coupling between an aldehyde and a Z vinyl iodide to assemble the two main fragments, a diastereoselective Myers alkylation, a stereoselective Evans aldolization, two asymmetric Duthaler crotyltitanations, and a stereoselective Pd-catalyzed Marshall allenylindium addition to install the stereogenic centers of dictyostatin. The synthesis of (9R)-epi-dictyostatin and a new ring-contracted dictyostatin isomer were also achieved. Copyright
Synthesis of the C1-C12 acid fragment of amphidinolide T marine macrolides via SmI2-mediated enantioselective reductive coupling of aldehydes with a chiral crotonate
Luo, Jialu,Li, Huoming,Wu, Jinlong,Xing, Xinglong,Dai, Wei-Min
experimental part, p. 6828 - 6833 (2009/12/06)
A new strategy for enantioselective assembly of the trisubstituted tetrahydrofuran ring has been established for synthesis of the C1-C12 acid fragment of amphidinolide T series marine macrolides. The key steps involve the SmI2-mediated highly e
Conformational analysis of axially substituted 4,4′-bi-1,3-dioxanyls
Brandl, Trixi,Hoffmann, Reinhard W.
, p. 4373 - 4378 (2007/10/03)
In contrast to the simple 4,4′-bi-1,3-dioxanyl derivative 6, which has no conformational preference at the inter-ring bond, the derivatives 9 and 10, which have two strategically placed axial methyl groups, show conformational preferences exceeding 95 %.
Synthesis of a Diels-Alder precursor for the Elisabethin A skeleton
Heckrodt, Thilo J.,Mulzer, Johann
, p. 1857 - 1866 (2007/10/03)
A synthesis of a precursor 2 for the Elisabethin A skeleton is reported. Containing a masked quinone and a (E,Z)-diene sub-unit, it has the required elements for the envisaged intramolecular Diels-Alder reaction to form the tricyclic system of Elisabethin A. Starting from methylresorcinol, the sequence involves the preparation of an arylacetic acid, which was α-alkylated by a chiral building block. Subsequent HWE reaction and cis-selective Wittig olefination furnished the diene with the desired geometry.
