1004519-87-2Relevant academic research and scientific papers
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.
Stereoselective total synthesis of dodoneine
Chinnababu, Baggu,Reddy, Sudina Purushotham,Rao, Chitturi Bhujanga,Rajesh, Karuturi,Venkateswarlu, Yenamandra
experimental part, p. 1960 - 1966 (2010/12/25)
A simple and highly efficient stereoselective total synthesis of dodoneine (1), a naturally occurring bioactive 5,6-dihydro-2H-pyran-2-one, was achieved. The synthesis involved Keck's asymmetric allylation, iodine-induced electrophilic cyclization, and Gr
Total synthesis of (+)-dodoneine and its 6-epimer
Sabitha, Gowravaram,Bhaskar, Vangala,Reddy, S. Siva Sankara,Yadav, Jhillu S.
experimental part, p. 3285 - 3292 (2010/03/01)
The total synthesis of dodoneine and its 6-epimer is described, using HKR of epoxide and reduction with SmI2 reactions as key steps, respectively.
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.
Stereoselective total synthesis of dodoneine
Das, Biswanath,Suneel, Kanaparthy,Satyalakshmi, Gandham,Kumar, Duddukuri Nandan
experimental part, p. 1536 - 1540 (2009/12/03)
The stereoselective total synthesis of the naturally occurring bioactive dihydropyranone dodoneine has been achieved involving the Sharpless asymmetric epoxidation, 1,3-syn diastereoselective reduction and Grubb's ring-closing metathesis as key steps.
Stereoselective synthesis of the naturally occurring 2-pyranone dodoneine
Alvarez-Bercedo, Paula,Falomir, Eva,Murga, Juan,Carda, Miguel,Marco, J. Alberto
experimental part, 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.
First stereoselective total synthesis of (+)-dodoneine
Srihari,Rajendar,Srinivasa Rao,Yadav
, p. 5590 - 5592 (2008/12/22)
The first stereoselective total synthesis of the natural product (+)-dodoneine is described involving a Crimmins aldol reaction and a Horner-Wadsworth-Emmons olefination as the key steps.
