1569-50-2Relevant articles and documents
Sneen,Bradley
, p. 6975,6981 (1972)
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Welch,S.C.,Walters,R.L.
, p. 2665 - 2673 (1974)
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Nesmejanow et al.
, (1958)
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Frankenfeld,Tyler
, p. 2110,2114 (1971)
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A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters
Albat, Dominik,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther
supporting information, p. 2099 - 2102 (2021/07/22)
A stereo-divergent synthesis of natural and unnatural opines in stereochemically pure form is based on the direct palladium-catalyzed N-allylation of α-amino acid esters (up to 97 % ee or 99 : 1 d.r.) using methyl (E)-2-penten-4-yl carbonate in the presence of only 1 mol% of a catalyst, prepared in-situ from the C2-symmetric diphosphine iPr-MediPhos and [Pd(allyl)Cl]2. Selected target compounds (incl. a derivative of the drug enalapril) were efficiently obtained from the N-allylated intermediates by oxidative cleavage (ozonolysis) of the allylic C=C bond under temporary N-Boc-protection.
Total synthesis of (+)-rubriflordilactone A
Goh, Shermin S.,Chaubet, Guilhem,Gockel, Birgit,Cordonnier, Marie-Caroline A.,Baars, Hannah,Phillips, Andrew W.,Anderson, Edward A.
supporting information, p. 12618 - 12621 (2015/10/28)
Two enantioselective total syntheses of the nortriterpenoid natural product rubriflordilactone A are described, which use palladium- or cobalt-catalyzed cyclizations to form the CDE rings, and converge on a late-stage synthetic intermediate. These key processes are set up through the convergent coupling of a common diyne component with appropriate AB-ring aldehydes, a strategy that sets the stage for the synthetic exploration of other members of this family of natural products. Two in one: Two enantioselective total syntheses of the nortriterpenoid natural product rubriflordilactone A are described, which use palladium- or cobalt-catalyzed cyclizations to converge on a late-stage synthetic intermediate. These key processes are set up through the coupling of a common diyne component with appropriate AB-ring aldehydes, a strategy that enables a broad exploration of this family of natural products, as well as synthetic analogues.
