85924-41-0Relevant academic research and scientific papers
Stereoselective ozonolysis of TMS-substituted allylic alcohol derivatives and synthesis of 14R,15 S - And 14 S,15 S-diHETE
Saito, Shun,Yamazaki, Takashi,Kobayashi, Yuichi
supporting information, p. 7636 - 7647 (2018/11/02)
Ozonolysis of TMS-substituted olefins produces α-carbonyl TMS peroxides without cleavage of the CC bond. Herein, stereochemistry in the ozonolysis was studied using silyl derivatives of (E)- and (Z)-(1-TMS)alk-1-en-3-ols. The (E)-isomers afforded the anti-3-siloxy-2-(TMS-oxy)aldehydes as the major stereoisomer (anti/syn = 3-9:1) after reductive work-up with Ph3P. In contrast, Z-olefins selectively gave the syn isomers with syn/anti ratios of 4-19:1. Facial selection was speculated based on the Cieplak effect. This ozonolysis was successfully applied for the synthesis of 14R,15S- and 14S,15S-diHETEs (anti and syn isomers, respectively) in enantioenriched forms.
Enantioselective synthesis of (10S)- and (10R)-methyl-anandamides
Nikas, Spyros P.,D'Souza, Marsha,Makriyannis, Alexandros
supporting information; experimental part, p. 6329 - 6337 (2012/09/08)
For the development of novel endocannabinoid templates with potential resistance to hydrolytic and oxidative metabolism, we are targeting the bis-allylic carbons of the arachidonoyl skeleton. Toward this end, we recently disclosed the synthesis and prelim
