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Total synthesis
About: Total synthesis is a research topic. Over the lifetime, 25578 publications have been published within this topic receiving 489319 citations.
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TL;DR: A formal synthesis of (+)-α-allokainic acid from an alkyne precursor was carried out by as mentioned in this paper using a short, efficient, and highly stereoselective approach.
Abstract: A formal synthesis of (+)-α-allokainic acid and a total synthesis of (−)-α-kainic acid were carried out using a short, efficient, and highly stereoselective approach. From an alkyne precursor, a nickel-catalyzed cyclization and a palladium-catalyzed rearrangement were utilized in the synthesis of (+)-α-allokainic acid. From an allene precursor, a nickel-catalyzed cyclization was utilized in the synthesis of (−)-α-kainic acid. The allene cyclization used in the latter sequence was the first example of a metal-catalyzed cyclization of this type.
85 citations
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TL;DR: A formal total synthesis of (±)-platensimycin [(±)-1] is reported in this article involving an intramolecular Stetter reaction and a radical cyclization.
85 citations
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TL;DR: An efficient total synthesis of (+)-vincristine has been accomplished through a stereoselective coupling of demethylvindoline and the eleven-membered carbomethoxyverbanamine presursor.
Abstract: An efficient total synthesis of (+)-vincristine has been accomplished through a stereoselective coupling of demethylvindoline and the eleven-membered carbomethoxyverbanamine presursor. Demethylvindoline was prepared by oxidation of 17-hydroxy-11-methoxytabersonine, followed by regioselective acetylation with mixed anhydride method. Although an initial attempt of coupling by using demethylvindoline formamide was not successful and resulted in recovery of the starting compounds, the reaction using demethylvindoline took place smoothly to furnish the desired bisindole product with the correct stereochemistry at C18′. After formation of the piperidine ring by sequential removal of the protective groups and intramolecular nucleophilic cyclization, the total synthesis of vincristine was completed by formylation of N1.
85 citations
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TL;DR: The total synthesis of several members of the hydroxylated phenanthridone subclass of the Amaryllidaceae alkaloid family has been carried out and the stereochemical outcome of the IMDAF cycloaddition has the side arm of the tethered vinyl group oriented exo with respect to the oxygen bridge.
Abstract: The total synthesis of several members of the hydroxylated phenanthridone subclass of the Amaryllidaceae alkaloid family has been carried out. (±)-Lycoricidine and (±)-7-deoxypancratistatin were assembled through a one-pot Stille/intramolecular Diels−Alder cycloaddition cascade to construct the core skeleton. The initially formed [4 + 2]-cycloadduct undergoes nitrogen-assisted ring opening followed by a deprotonation/reprotonation of the resulting zwitterion to give a rearranged hexahydroindolinone on further heating at 160 °C. The stereochemical outcome of the IMDAF cycloaddition has the side arm of the tethered vinyl group oriented exo with respect to the oxygen bridge. The resulting cycloadduct was used for the stereocontrolled installation of the remaining functionality present in the C-ring of the target molecules. Key features of the synthetic strategy include (1) a lithium hydroxide induced tandem hydrolysis/decarboxylation/elimination sequence to introduce the required π-bond in the C-ring of (±)-...
85 citations