104713-29-3Relevant academic research and scientific papers
Trifunctional Chiral Synthons via Stereocontrolled Yeast Reduction. Preparation of Chiral Pentane-1,3,5-triol Derivatives
Hirama, Masahiro,Nakamine, Takeshi,Ito, Sho
, p. 1381 - 1384 (1986)
Easy access to pentane-1,3,5-triol derivatives of high optical purity, trifunctional chiral synthons of fundamental importance in the synthesis of various natural products is described, as well as the stereocontrol of baker's yeast reduction of 5-substituted 3-oxopentanoates.
The enantioselective synthesis of simplified southern-half fragments of soraphen A
Loubinoux, Bernard,Sinnes, Jean-Luc,O'Sullivan, Anthony C.,Winkler, Tammo
, p. 3549 - 3558 (1995)
The compound 2 comprises a southern-half subunit of the fungicidal macrolide soraphen A 1. It was prepared by a Meinwald reaction of the enolate of S-7 with the lactone S-8. Its enantiomer and diastereomers were synthesized in a similar manner. The lacton
An efficient strategy for the synthesis of syn 1,3-diols via iterative acetate aldol reactions and synthesis of atorvastatin lactone
Goyal, Sandeep,Patel, Bhautikkumar,Sharma, Ratnesh,Chouhan, Mangilal,Kumar, Kapil,Gangar, Mukesh,Nair, Vipin A.
, p. 5409 - 5412 (2015/09/15)
An efficient strategy for the synthesis of syn 1,3-diol has been developed, employing an imidazolidinone based chiral auxiliary via stereoselective and sequential double acetate aldol reactions. The syn 1,3-diol subunit was modified to obtain the C-7 carboxylic acid side chain and further subjected to reaction with a suitable 1,4-diketone under Paal-Knorr conditions to obtain atorvastatin lactone.
Development of Chiral Spiro P-N-S Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of β-Alkyl-β-Ketoesters
Bao, Deng-Hui,Wu, Hui-Ling,Liu, Chao-Lun,Xie, Jian-Hua,Zhou, Qi-Lin
supporting information, p. 8791 - 8794 (2015/11/27)
The chiral tridentate spiro P-N-S ligands (SpiroSAP) were developed, and their iridium complexes were prepared. Introduction of a 1,3-dithiane moiety into the ligand resulted in a highly efficient chiral iridium catalyst for asymmetric hydrogenation of β-alkyl-β-ketoesters, producing chiral β-alkyl-β-hydroxyesters with excellent enantioselectivities (95-99.9 % ee) and turnover numbers of up to 355 000. Bulkyness is the key: New chiral tridentate spiro P-N-S ligands (SpiroSAP) bearing a conformationally constrained 1,3-dithiane moiety were developed. Their iridium catalysts showed excellent enantioselectivities and activity (TON up to 355 000) for asymmetric hydrogenation of β-alkyl-β-ketoesters.
Tetrahydropyran synthesis by intramolecular conjugate addition to enones: Synthesis of the clavosolide tetrahydropyran ring
Bates, Roderick W.,Song, Ping
experimental part, p. 2935 - 2942 (2010/10/21)
The synthesis of a tetrahydropyran intermediate for clavosolide A is reported, employing a combination of cross-metathesis and intramolecular oxa-Michael addition. The intramolecular oxa-Michael addition to ,-unsaturated esters requires the use of strong bases and can result in either modest yields or stereoisomeric mixtures, and can be highly variable according to the substrate structure. In contrast, the corresponding ketones cyclise under very mild conditions to give the 2,6-cis-isomers directly. The use of appropriately substituted ketones allows efficient conversion into esters.
The synthesis of single enantiomers of mycobacterial ketomycolic acids containing cis-cyclopropanes
Koza, Gani,Theunissen, Cornelia,Al Dulayymi, Juma'a R.,Baird, Mark S.
experimental part, p. 10214 - 10229 (2010/02/28)
We report the syntheses of a single enantiomer of an unprotected ketomycolic acids containing a cis-cyclopropane and of related hydroxy-mycolic acids.
A General Method for the Synthesis of Both Enantiomers of Optically Pure β-Hydroxy Esters from (S)-(p-Chlorophenylsulfinyl)acetone Easily Obtainable by Kinetic Resolution with Bakers' Yeast
Fujitsawa, Tamotsu,Fujimura, Atsushi,Sato, Toshio
, p. 1273 - 1280 (2007/10/02)
Both enantiomers of various optically pure (R)- and (S)-β-hydroxy esters were generally synthesized from (S)-(p-chlorophenylsulfinyl)acetone obtained by kinetic resolution with bakers' yeast, followed by γ-alkylation, diastereoselective reduction, subsequent introduction of ester group and reductive elimination of the sulfinyl group.The key step of the diastereoselective reduction of (S)-β-keto sulfoxides was performed with diisobutylaluminum hydride to give (R)C-(S)S-β-hydroxy sulfoxides or after complexation with zinc chloride followed by addition of diisobutylaluminum hydride to give (S)C-(S)S-β-hydroxy sulfoxides which were easily separated in an optically pure form by easy crystallization or separation by silica-gel chromatography due to the p-chlorophenyl moiety in the β-hydroxy sulfoxides.The utility of the present method could be successfully demonstrated in the synthesis of both (+)- and (-)-corynomycolic acids from optically pure methyl esters of (R)- and (S)-3-hydroxyoctadecanoic acid by alkylation with tetradecyl iodide at α-position and hydrolysis.
