169775-23-9Relevant academic research and scientific papers
Catalytic Asymmetric Crotylation of Aldehydes: Application in Total Synthesis of (-)-Elisabethadione
O'Hora, Paul S.,Incerti-Pradillos, Celia A.,Kabeshov, Mikhail A.,Shipilovskikh, Sergei A.,Rubtsov, Aleksandr E.,Elsegood, Mark R. J.,Malkov, Andrei V.
supporting information, p. 4551 - 4555 (2015/03/18)
A new, highly efficient Lewis base catalyst for a practical enantio- and diastereoselective crotylation of unsaturated aldehydes with E- and Z-crotyltrichlorosilanes has been developed. The method was employed as a key step in a novel asymmetric synthesis of bioactive serrulatane diterpene (-)-elisabethadione. Other strategic reactions for setting up the stereogenic centers included anionic oxy-Cope rearrangement and cationic cyclization. The synthetic route relies on simple, high yielding reactions and avoids use of protecting groups or chiral auxiliaries.
Formal synthesis of 7-methoxymitosene and synthesis of its analog via a key PtCl2-catalyzed cycloisomerization
Liu, Lianzhu,Wang, Yanzhao,Zhang, Liming
supporting information; experimental part, p. 3736 - 3739 (2012/09/21)
A formal synthesis of 7-methoxymitosene is achieved via a key platinum-catalyzed cycloisomerization. The precursor for the Pt catalysis, a fully functionalized benzene intermediate, was prepared via a regioselective electrophilic bromination followed by a
Gold(I)-catalyzed intramolecular [4+2] cycloadditions of arylalkynes or 1,3-enynes with alkenes: Scope and mechanism
Nieto-Oberhuber, Cristina,Perez-Galan, Patricia,Herrero-Gomez, Elena,Lauterbach, Thorsten,Rodriguez, Cristina,Lopez, Salome,Bour, Christophe,Rosellon, Antonio,Cardenas, Diego J.,Echavarren, Antonio M.
, p. 269 - 279 (2008/09/20)
The cyclizations of enynes substituted at the alkyne gives products of formal [4+2] cyclization with Au(I) catalysts. 1,8-Dien-3-ynes cyclize by a 5-exo-dig pathway to form hydrindanes. 1,6-Enynes with an aryl ring at the alkyne give 2,3,9,9a-tetrahydro-1
Stereocontrolled synthesis of C-arylglycosides applied to the south west fragment of the antibiotic kendomycin
Marques, Maria M. B.,Pichlmair, Stefan,Martin, Harry J.,Mulzer, Johann
, p. 2766 - 2770 (2007/10/03)
A nine step synthesis of the southwest fragment 3 of the antibiotic kendomycin (1) is reported. The tetrahydropyran ring is prepared in a highly stereocontrolled and efficient sequence. The key step concerns an anti-aldol reaction using chiral ketone 10. C-Aryl glycoside 3 exhibits atropisomerism and the relative configuration around its tetrahydropyran ring was established by NOE experiments.
Biaryl formation using the Suzuki protocol: Considerations of base, halide, and protecting group
Benbow, John W.,Martinez, Bonnie L.
, p. 8829 - 8832 (2007/10/03)
The generation of aryl anions prior to quenching with a trialkyl berate has been shown to be sensitive to the composition of the aryl substrate. Aryl iodides containing remote benzyl ether substituents undergo trans-metallation with sec-BuLi to cleanly give the desired aryl anions whereas the corresponding bromides afford appreciable quantities of dianionic intermediates. The aryl boronic acids derived from alkylation of these anions subsequently undergo a palladium mediated coupling with aryl halides to provide good yields of the desired biaryls. Copyright (C) 1996 Elsevier Science Ltd.
