82263-60-3Relevant 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
, 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.
ON THE SYNTHESIS AND STRUCTURE OF LIPOXIN B
Corey, E. J.,Mehrotra, Mukund M.,Su, Wei-guo
, p. 1919 - 1922 (2007/10/02)
A synthesis of lipoxin B, a recently discovered biologically active eicosanoid, and the assignment of stereoformula 2 is reported.
