3796-62-1Relevant academic research and scientific papers
Stereoselective Directed Cationic Cascades Enabled by Molecular Anchoring in Terpene Cyclases
Schneider, Andreas,Jegl, Philipp,Hauer, Bernhard
supporting information, p. 13251 - 13256 (2021/04/30)
Cascade reactions appeared as a cutting-edge strategy to streamline the assembly of complex structural scaffolds from naturally available precursors in an atom-, as well as time, labor- and cost-efficient way. We herein report a strategy to control cation
First synthesis of achilleol A using titanium(III) chemistry
Barrero, Alejandro F,Cuerva, Juan M,Alvarez-Manzaneda,Oltra, J.Enrique,Chahboun, Rachid
, p. 2793 - 2796 (2007/10/03)
Described herein is a straightforward synthesis of the monocyclic triterpene achilleol A using as key step titanium(III) chemistry. This synthesis confirms the previously described structure based on spectroscopic methods.
Selective rhenium-catalyzed oxidation of secondary alcohols with methyl sulfoxide in the presence of ethylene glycol, a convenient one-pot synthesis of ketals
Arterburn, Jeffrey B.,Perry, Marc C.
, p. 769 - 771 (2008/02/12)
Formula presented Secondary alcohols are oxidized preferentially by DMSO and the catalyst ReOCl3(PPh3)2 in the presence of ethylene glycol and refluxing toluene, producing the corresponding ketals. The reactions are rapid, and proceed in very good to excellent yields. The byproducts of the reaction, methyl sulfide and water, are easily removed. No epoxidation or other common side reactions were observed. This direct oxidative transformation of alcohols to the protected ketal derivatives should have broad synthetic applicability.
Studies on macrocyclic diterpenoids (XVII): Total synthesis of (-)-cembrene-A and (+)-3,4-epoxycembrene-A by titanium-induced carbonyl coupling reactions
Yue, Xiangjun,Li, Yulin
, p. 736 - 740 (2007/10/03)
Efficient total syntheses of (R)-cembrene-A (1) and (+)-3,4-epoxycembrene-A (2), two marine cembranoids, starting from (E)-geranylacetone (6) and (R)-limonene (7) are described. The key steps are the synthesis of olefin 12 from phosphonate 4 and optically active ketone 5 by the modified Wittig olefination, and the titanium-induced intramolecular coupling of oxo aldehyde 3 to afford cembrene-A (1). The pinacol coupling of 3 yielded the diol 13 which was converted into 3,4-epoxycembrene-A (2).
