122151-32-0Relevant articles and documents
Efficient Stereoselective Synthesis of a Key Chiral Aldehyde Intermediate in the Synthesis of Picolinamide Fungicides
Li, Fangzheng,Good, Steffen,Tulchinsky, Michael L.,Whiteker, Gregory T.
, p. 2253 - 2260 (2019)
A highly stereoselective and efficient synthesis of (4S,5S,6S)-6-(benzyloxy)-5-phenoxy-4-propoxyheptanal, a key intermediate for syntheses of picolinamide fungicides, is described in this report. The synthesis features a scalable allylpropyl ether preparation, an efficient synthesis of the C1-C3 anti,syn-(S,S,S) stereotriad via a highly diastereoselective allylboration, and Cu-catalyzed phenylation of a sterically hindered secondary alcohol with BiPh3(OAc)2 followed by highly regioselective hydroformylation with the formation of a linear aldehyde. Excellent overall route efficiency was achieved (six steps and 39% yield) starting from readily available and inexpensive (S)-ethyl lactate.
Toward Chromanes by de Novo Construction of the Benzene Ring
Geist, Egor,Berneaud-K?tz, Helge,Baikstis, Tomas,Dr?ger, Gerald,Kirschning, Andreas
supporting information, p. 8930 - 8933 (2019/11/14)
The work describes three principal Diels-Alder cycloaddition approaches toward chromanes that are designed for the de novo construction of the benzene ring. This study specifically focuses on the potential exploitation in the total synthesis of chromane-bearing natural products such as cebulactam A.
A PROCESS FOR THE MANUFACTURE OF POSACONAZOLE
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Page/Page column 12; 15, (2019/05/10)
The present invention discloses an improved process for the manufacture of Posaconazole, an anti-fungal agent belonging to the category of substituted Tetrahydrofuran Triazole compound. The present invention further describes preparation of formula A and formula B, the key intermediates in the preparation of Posaconazole. The invention also discloses novel intermediates that are useful in the synthesis of Posaconazole.
Total synthesis of (+)-herboxidiene/GEX 1A
Gómez-Palomino, Alejandro,Pellicena, Miquel,Kr?mer, Katrina,Romea, Pedro,Urpí, Fèlix,Aullón, Gabriel,Padrón, José M.
, p. 1842 - 1862 (2017/03/09)
A total synthesis of (+)-herboxidiene/GEX 1A has been accomplished from (R)- and (S)-lactate esters in a highly efficient manner. Key steps of the synthesis involve substrate-controlled titanium-mediated aldol reactions from chiral lactate-derived ethyl ketones, an oxa-Michael cyclization, an Ireland-Claisen rearrangement, and a Suzuki coupling. Furthermore, computational studies of the oxa-Michael reaction have unveiled the dramatic influence of intramolecular hydrogen bonds on the stereochemical outcome of such cyclizations, whereas biological analyses have clearly proved the important cytoxicity of (+)-herboxidiene/GEX 1A.
Stereoselective titanium-mediated aldol reactions of α-benzyloxy methyl ketones
Pellicena, Miquel,Solsona, Joan G.,Romea, Pedro,Urpi, Felix
, p. 10338 - 10350,13 (2012/12/12)
Good levels of 1,4-anti asymmetric induction are obtained in the TiCl 3(i-PrO)-mediated aldol reaction of chiral α-benzyloxy methyl ketones with a wide array of aldehydes. This methodology represents a new approach to substrate-controlled acetate aldol reactions capable of providing highly functionalized fragments in a straightforward manner, which may be useful in the design of more efficient syntheses.
Stereoselective titanium-mediated aldol reactions of α-benzyloxy methyl ketones
Pellicena, Miquel,Solsona, Joan G.,Romea, Pedro,Urpí, Fèlix
, p. 10338 - 10350 (2013/01/15)
Good levels of 1,4-anti asymmetric induction are obtained in the TiCl 3(i-PrO)-mediated aldol reaction of chiral α-benzyloxy methyl ketones with a wide array of aldehydes. This methodology represents a new approach to substrate-controlled acetate aldol reactions capable of providing highly functionalized fragments in a straightforward manner, which may be useful in the design of more efficient syntheses.
Simple and efficient preparation of enantiopure alkyl α-hydroxyalkyl ketones
Ferrero,Galobardes,Martin,Montes,Romea,Rovira,Urpi,Vilarrasa
, p. 1608 - 1614 (2007/10/03)
The acylation reaction of organolithium reagents with pyrrolidine-derived α-benzyloxy and α-silyloxy carboxamides provides a simple and high-yielding method for the preparation of enantiopure α-benzyloxy and α-silyloxy ketones.
A simple procedure for the preparation of enantiopure ethyl α-hydroxyalkyl ketones
Martin, Ricardo,Pascual, Oscar,Romea, Pedro,Rovira, Roser,Urpi, Felix,Vilarrasa, Jaume
, p. 1633 - 1636 (2007/10/03)
Amides derived from pyrrolidine and methyl (S)-lactate, methyl (S)-2-hydroxy-3-phenylpropanoate, or methyl (S)-2-hydroxy-3-methylbutanoate, after O-benzylation and O-silylation have been treated with EtLi or EtMgCl under suitable conditions, to give excellent overall yields of enantiopure ethyl ketones. The chelating ability of α-OBn amides (and even of α-O-TBS amides, which has been demonstrated by NMR to be better than that of N-OMe amides) accounts for the performance of the approach.
