256494-32-3Relevant academic research and scientific papers
Total stereocontrolled synthesis of a novel pyrrolizidine iminosugar
De Angelis, Martina,Primitivo, Ludovica,Lizzio, Federica,Agostinelli, Sonia,Sappino, Carla,Ben Romdan, Ilaria,Bonanni, Luciano,D'Annibale, Andrea,Antonioletti, Roberto,Ricelli, Alessandra,Righi, Giuliana
, (2021/12/20)
Herein we describe a versatile approach to the pyrrolizidine alkaloids skeleton by tailoring our original strategy already used for the pyrrolidine iminosugars synthesis. The key steps are the regio- and stereoselective azidolysis of the suitable chiral v
Divergent syntheses of resorcylic acid lactones: L-783277, LL-Z1640-2, and hypothemycin
Dakas, Pierre-Yves,Jogireddy, Rajamalleswaramma,Valot, Gaelle,Barluenga, Sofia,Winssinger, Nicolas
supporting information; experimental part, p. 11490 - 11497 (2010/04/28)
The resorcylic acid lactones (RAL) are endowed with diverse biological activity ranging from transcription factor modulators (zearalenone and zearalenol) to HSP90 inhibitors (radicicol and pochonin D) and reversible (aigialomycin D) as well as irreversibl
Total syntheses of amphidinolide X and Y
Fuerstner, Alois,Kattnig, Egmont,Lepaqe, Olivier
, p. 9194 - 9204 (2007/10/03)
Concise total syntheses of the cytotoxic marine natural products amphidinolide X (1) and amphidinolide Y (2) as well as of the nonnatural analogue 19-epi-amphidinolide X (47) are described. A pivotal step of the highly convergent routes to these structurally rather unusual secondary metabolites consists of a syn-selective formation of allenol 17 by an iron-catalyzed ring opening reaction of the enantioenriched propargyl epoxide 16 (derived from a Sharpless epoxidation) with a Grignard reagent. Allenol 17 was then cyclized with the aid of Ag(I) to give dihydrofuran 19 containing the (R)-configured tetrasubstituted sp3 chiral center at C. 19, which was further elaborated into tetrahydrofuran 25 representing the common heterocyclic motif of 1 and 2. The aliphatic chain of amphidinolide X featuring an anti-configured stereodiad at C. 10 and C. 11 was generated by a palladium-catalyzed, Et 2Zn-promoted addition of the enantiopure propargyl mesylate 29 to the functionalized aldehyde 28. The preparation of the corresponding C.1-C.12 segment of amphidinolide Y relies on asymmetric hydrogenation of an α-ketoester, a diastereoselective boron aldol reaction, and a chelate-controlled addition of MeMgBr in combination with suitable oxidation state management for the elaboration of the tertiary acyloin motif. Importantly, the end games of both total syntheses follow similar blueprints, involving key fragment coupling processes via the "9-MeO-9-BBN" variant of the alkyl-Suzuki reaction and final Yamaguchi esterifications to forge the 16-membered macrodiolide ring of amphidinolide X and the 17-membered macrolide frame of amphidinolide Y, respectively. This methodological convergence ensures high efficiency and an excellent overall economy of steps for the entire synthesis campaign.
Total synthesis of amphidinolide X
Lepage, Olivier,Kattnig, Egmont,Fuerstner, Alois
, p. 15970 - 15971 (2007/10/03)
A concise total synthesis of the cytotoxic marine natural product amphidinolide X (1) is described. A key step of the highly convergent route to this structurally rather unusual macrodiolide derivative consists of a newly developed, highly syn selective f
Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes
Nacro,Baltas,Gorrichon
, p. 14013 - 14030 (2007/10/03)
Aldol condensations on α,β-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and syn γ,δ-epoxy β-hyd
