461406-52-0Relevant academic research and scientific papers
Ketyl radical cyclization of β-disubstituted acrylates: Formal syntheses of (+)-secosyrin 1 and longianone and the total synthesis of (+)-4-epi-secosyrin 1
Donner, Christopher D.
supporting information, p. 1258 - 1261 (2013/05/09)
A novel approach to the synthesis of a series of 1,7-dioxaspirononanes that applies a ketyl radical cyclization strategy is described. Radical cyclization of the β-disubstituted acrylate 23, prepared in five steps from (R)-1,2-isopropylideneglycerol, gives both 2,3-syn- and 2,3-anti-furan products. The densely functionalized furan heterocycles are used to complete a concise formal synthesis of secosyrin 1, a metabolite of Pseudomonas syringae, and the total synthesis of 4-epi-secosyrin 1.
Absolute configuration and total synthesis of a novel antimalarial lipopeptide by the de novo preparation of chiral nonproteinogenic amino acids
Ghosh, Shibaji K.,Somanadhan, Brinda,Tan, Kevin S.-W.,Butler, Mark S.,Lear, Martin J.
supporting information; scheme or table, p. 1560 - 1563 (2012/06/16)
The absolute configuration (via degradation and Marfey's derivatization studies) and the total synthesis of a novel antimalarial lipid-peptide isolated from Streptomyces sp. (IC50 = 0.8 μM, Plasmodium falciparum 3D7) is disclosed. To this end, versatile stereocontrolled routes to nonproteinogenic amino acids (via catalytic Mannich, Sharpless methods) and enantiomeric trans fatty acids (via Evans alkylation, Kocienski-Julia olefination) have been developed.
Synthesis of enantiopure 2-C-methyl-d-erythritol-4-phosphate
Raghavan, Sadagopan,Sreekanth
, p. 9090 - 9092 (2008/09/16)
The synthesis of enantiopure 2-C-methyl-d-erythritol-4-phosphate is disclosed. A 1,3-diol possessing a quaternary stereogenic centre, prepared stereoselectively from an acyclic tri-substituted alkene, has been utilized as a key intermediate.
Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin
Fukuzaki, Takehiro,Kobayashi, Satoshi,Hibi, Takamasa,Ikuma, Yohei,Ishihara, Jun,Kanoh, Naoki,Murai, Akio
, p. 2877 - 2880 (2007/10/03)
(figure presented) Studies on the connection between the right and left segments of azadirachtin are described. The Ireland-Claisen rearrangement of Li-enolate of the modeled ester with dichlorodimethylsilane in toluene afforded the desired limonoid frame
