74066-96-9Relevant articles and documents
Asymmetric Construction of Alkaloids by Employing a Key ω-Transaminase Cascade
Taday, Freya,Ryan, James,Argent, Stephen P.,Caprio, Vittorio,Maciá, Beatriz,O'Reilly, Elaine
supporting information, p. 3729 - 3732 (2020/03/11)
An ω-transaminase-triggered intramolecular aza-Michael reaction has been employed for the preparation of cyclic β-enaminones in good yield and excellent enantio- and diastereoselectivity, starting from easily accessible prochiral ketoynones and commercially available enzymes. The powerful thermodynamic driving force associated with the spontaneous aza-Michael reaction effectively displaces the transaminase reaction equilibrium towards product formation, using only two equivalents of isopropylamine. To demonstrate the potential of this methodology, this biocatalytic aza-Michael step was combined with annulation chemistry, affording unique stereo-defined fused alkaloid architectures.
Identification and synthesis of volicitin and related components from beet armyworm oral secretions
Alborn,Jones,Stenhagen,Tumlinson
, p. 203 - 220 (2007/10/03)
Oral secretion of beet armyworm caterpillars (BAW), when applied to damaged tissues of corn seedlings, induces the seedlings to emit volatile compounds that attract the natural enemies of the caterpillars. The key elicitor present in BAW oral secretions is N-[17-hydroxylinolenoyl]-L- glutamine (volicitin). Analysis of the oral secretion showed that it also contained N-[17-hydroxyolinoleoyl]-L-glutamine, free 17-hydroxylinolenic, and 17-hydroxylinoleic acid, the glutamine conjugates of linolenic and linoleic acid as well as free linolenic and linoleic acid. Here we present the identification and synthesis of the hydroxy acids and of glutamine conjugates.
Metal-Catalyzed Organic Photoreactions. Bond-Cleavage Selectivity and Synthetic Application of the Iron(III) Chloride Catalyzed Photooxidation of Cyclic Olefins
Kohda, Akira,Nagayoshi, Kazuo,Maemoto, Kazuo,Sato, Tadashi
, p. 425 - 432 (2007/10/02)
Photooxidation of olefins in pyridine in the presence of iron(III) chloride produced either α-chloro ketones (type A), gem-dichloro ketones (type B), or α,ω-dichloro ketones (type C), depending upon the substitution pattern of the substrate olefin.The synthetic utility of the type B reaction was demonstrated by the synthesis of some natural products.The synthesis of optically active solanone from D-p-menthene confirmed the D configuration of the natural product.