622397-33-5Relevant academic research and scientific papers
Lewis acid catalyzed synthesis of cyclic carbonates, precursors of 1,2- and 1,3-diols
Cornil, Johan,Gonnard, Laurine,Guerinot, Amandine,Reymond, Sebastien,Cossy, Janine
supporting information, p. 4958 - 4962 (2014/08/18)
An eco-friendly synthesis of cyclic carbonates through a Lewis acid catalyzed cyclization of tert-butyl carbonates is described. These cyclic carbonates are precursors of 1,2- and 1,3-diols, and the developed method was applied to a short synthesis of a diarylheptanoid, (3S,5S)-alpinikatin.
Enantioselective total synthesis of (-)-ericanone
Dias, Luiz C.,Kuroishi, Paula K.,Polo, Ellen C.,De Lucca Jr., Emílio C.
supporting information, p. 980 - 982 (2013/02/25)
The first total synthesis of (-)-ericanone was achieved in 10 steps with a 16% overall yield from p-hydroxybenzaldehyde. Notable features of this stereocontrolled approach include a Keck allylation to install the stereocenter at C3 and a 1,5-anti aldol reaction to install the hydroxyl group at C7.
Stereoselective total synthesis of (+)-dodoneine
Allais, Florent,Ducrot, Paul-Henri
experimental part, p. 1649 - 1653 (2010/06/20)
A total synthesis of the naturally occurring dihydropyranone dodoneine is reported. The combination of a highly catalytic enantioselective allylboration and a highly diastereoselective allylstannation was used for the stereoselective generation of the two stereogenic centers. The pyranone ring was created in two steps through generation of a Z-configured ,-unsaturated ester and lactonization via intramolecular transesterification. Georg Thieme Verlag Stuttgart.
Rationally improved chiral Bronsted acid for catalytic enantioselective allylboration of aldehydes with an expanded reagent scope
Rauniyar, Vivek,Hall, Dennis G.
supporting information; experimental part, p. 4236 - 4241 (2009/09/30)
(Chemical Equation Presented) One of the most useful reactions in organic synthesis, the stereocontrolled addition of allylic metal reagents to carbonyl compounds, provides access to enantiomerically enriched homoallylic alcohols related to the acetate, propionate, and other oxygen-containing functionalities present in a large number of biologically active natural products and pharmaceutical drugs. In the search for an ideal carbonyl allylation methodology, the catalytic enantioselective allylboration presents numerous advantages such as a high chemo-, diastereo-, and enantiocontrol with stable and nontoxic pinacol allylic boronates. This article reports a rationally improved diol·SnCl4 complex as chiral protic acid catalyst, which provides unprecedented levels of enantioselectivity in the catalytic allylation, methallylation, crotylation, and 2-bromoallylation of aliphatic aldehydes. The new diol, p-F-Vivol (4b), enables a more active diol·SnCl4 catalyst that can compete more effectively with the background uncatalyzed allylboration. The usefulness of this optimized catalytic allylboration methodology was demonstrated with an efficient synthesis of the naturally occurring pyranone (+)-dodoneine and to the preparation of biologically important exomethylene-γ-lactones.
A stereodivergent synthesis of all stereoisomers of centrolobine: Control of selectivity by a protecting-group manipulation
Schmidt, Bernd,Hoelter, Frank
experimental part, p. 11948 - 11953 (2010/05/18)
All stereoisomers of the natural product centrolobine are selectively synthesized, by starting from a common precursor. Key steps are an enantioselective allylation with enantiomerically pure allylsilanes, a tandem ring-closing metathesis-isomerization re
Stereoselective synthesis of the naturally occurring 2-pyranone dodoneine
Alvarez-Bercedo, Paula,Falomir, Eva,Murga, Juan,Carda, Miguel,Marco, J. Alberto
body text, p. 4015 - 4018 (2009/04/11)
The first total synthesis of the naturally occurring dihydropyranone dodoneine is reported. Asymmetric allylation reactions were used for the stereoselective generation of the two stereogenic centers. The pyranone ring was created by ring-closing metathes
Total synthesis of (+)-dodoneine
Dittoo, Aurélia,Bellosta, Véronique,Cossy, Janine
body text, p. 2459 - 2460 (2009/05/07)
An eight-step synthesis of (+)-dodoneine was achieved from methyl 3-(4-hydroxyphenyl)propionate. Georg Thieme Verlag Stuttgart.
Stereoselective Construction of cis-2,6-Disubstituted Tetrahydropyrans via the Reductive Etherification of δ-Trialkylsilyloxy Substituted Ketones: Total Synthesis of (-)-Centrolobine
Evans, P. Andrew,Cui, Jian,Gharpure, Santosh J.
, p. 3883 - 3885 (2007/10/03)
(Matrix presented). The stereoselective intramolecular reductive etherification of δ-trialkylsilyloxy substituted ketones with catalytic bismuth tribromide and trielhylsilane provides a convenient method for the construction of cis-2,6-disubstituted tetra
