105405-22-9Relevant academic research and scientific papers
A unifying synthesis approach to the C18-, C19-, and C20-diterpenoid alkaloids
Kou, Kevin G. M.,Kulyk, Svitlana,Marth, Christopher J.,Lee, Jack C.,Doering, Nicolle A.,Li, Beryl X.,Gallego, Gary M.,Lebold, Terry P.,Sarpong, Richmond
, p. 13882 - 13896 (2017)
The secondary metabolites that comprise the diterpenoid alkaloids are categorized into C18, C19, and C20 families depending on the number of contiguous carbon atoms that constitute their central framework. Herein, we detail our efforts to prepare these molecules by chemical synthesis, including a photochemical approach, and ultimately a bioinspired strategy that has resulted in the development of a unifying synthesis of one C18 (weisaconitine D), one C19 (liljestrandinine), and three C20 (cochlearenine, paniculamine, and N-ethyl-1α-hydroxy-17-veratroyldictyzine) natural products from a common intermediate.
Effect of protic additives in Cu-catalysed asymmetric Diels-Alder cycloadditions of doubly activated dienophiles: Towards the synthesis of magellanine-type: Lycopodium alkaloids
Lindsay, Vincent N. G.,Murphy, Rebecca A.,Sarpong, Richmond
, p. 10291 - 10294 (2017)
The pronounced beneficial effect of a precise amount of protic additive in an enantioselective Cu-catalysed Diels-Alder reaction is reported. This reaction, which employs a cyclic alkylidene β-ketoester as a dienophile, represents one of the first example
Synthetic efforts toward the Lycopodium alkaloids inspires a hydrogen iodide mediated method for the hydroamination and hydroetherification of olefins
Leger, Paul R.,Murphy, Rebecca A.,Pushkarskaya, Eugenia,Sarpong, Richmond
supporting information, p. 4377 - 4383 (2015/03/14)
Progress toward the total syntheses of a diverse set of fawcettimine-type Lycopodium alkaloids via a "Heathcock-type" 6-5-9 tricycle is disclosed. This route features an intermolecular Diels-Alder cycloaddition to rapidly furnish the 6-5-fused bicycle and a highly chemoselective directed hydrogenation to build the azonane fragment. While conducting these synthetic studies, trimethylsilyl iodide was found to effect a hydroamination reaction to furnish the tetracyclic core of serratine and related natural products. This observation has been expanded into a general method for the room temperature hydroamination of unactivated olefins with tosylamides utilizing catalytic "anhydrous" HI (generated in situ from trimethylsilyl iodide and water). The presence of the iodide anion is critical to the success of this Bronsted acid catalyzed protocol, possibly due to its function as a weakly coordinating anion. These conditions also effect the analogous hydroetherification reaction of alcohols with unactivated olefins.
Palladium-catalyzed dehydrogenative β′-arylation of β-keto esters under aerobic conditions: Interplay of metal and Bronsted acids
Yip, Kai-Tai,Nimje, Roshan Y.,Leskinen, Mikko V.,Pihko, Petri M.
supporting information, p. 12590 - 12594 (2012/11/13)
The Bronsted aids: The first dehydrogenative arylation of β-keto esters with arenes under ambient aerobic conditions is described (see scheme). Under a PdII/Bronsted acid co-catalytic system, regioselective arylations with alkoxylated arenes an
Synthesis of the bridging framework of phragmalin-type limonoids
Lebold, Terry P.,Gallego, Gary M.,Marth, Christopher J.,Sarpong, Richmond
supporting information; experimental part, p. 2110 - 2113 (2012/07/03)
An efficient synthesis of the octahydro-1H-2,4-methanoindene core of phragmalin-type limonoids, such as xyloccensins O and P, is reported. The success of the synthetic route is predicated on the use of network analysis in the retrosynthetic analysis and a
