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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: The first enantioselective total synthesis of (-)-asperdiol has been accomplished in 15 steps from epoxygeranyl bromide as mentioned in this paper, which is the first complete synthesis of a cembranoid.
Abstract: The first enantioselective total synthesis of (-)-asperdiol has been accomplished in 15 steps from epoxygeranyl bromide. It is noteworthy that the trisubstituted epoxide was robust enough to survive the conditions for the nucleophilic displacement reactions which were used to form the C-12, C-13 and the '2-3, C-4 bonds. The epoxide also survived the reductive desulfonylation and the intramolecular Horner-Emmons reaction. Our assumption that the cyclization to the 14-membered ring in the desepoxy series would be more straightfoward than in the epoxy series, which provided the impetus for the synthesis of (+)-desepoxyasperdiol, was shown to be false. A number of the optically pure fragments which were used for the total synthesis of 1, particularly 4 and 7, will be useful for the synthesis of other cembranoids.
95 citations
TL;DR: The first total synthesis of (+/-)-psychotrimine, a novel trimeric indole alkaloid isolated from Psychotria rostrata, was achieved.
95 citations
TL;DR: Several synthetic intermediates and spirotryprostatin analogs were tested for their activity as G2/M phase cell cycle inhibitors and microtuble assembly against 3Y1 and tsFT210 mammalian cells.
95 citations
TL;DR: Through the preparation of these compounds, the utility of constructing benzylic quaternary stereogenic centers, even those lacking a carbonyl group in the α-position, by asymmetric α-arylation is demonstrated.
Abstract: We report a concise, enantioselective total synthesis of (−)-taiwaniaquinone H and the first enantioselective total synthesis of (−)-taiwaniaquinol B by a route that includes asymmetric palladium-catalyzed α-arylation of a ketone with an aryl bromide that was generated by sterically controlled halogenation via iridium-catalyzed C−H borylation. This asymmetric α-arylation creates the benzylic quaternary stereogenic center present in the taiwaniaquinoids. The synthesis was completed efficiently by developing a Lewis acid-promoted cascade to construct the [6,5,6] tricyclic core of an intermediate common to the synthesis of a number of taiwaniaquinoids. Through the preparation of these compounds, we demonstrate the utility of constructing benzylic quaternary stereogenic centers, even those lacking a carbonyl group in the α-position, by asymmetric α-arylation.
94 citations
TL;DR: The diastereoselective addition of the highly functionalized organozinc compound 1 to the aldehyde 2 in the presence of the chiral amino alcohol 3 (-->4) is a key step in the first total synthesis of (+)-halichlorine.
Abstract: The diastereoselective addition of the highly functionalized organozinc compound 1 to the aldehyde 2 in the presence of the chiral amino alcohol 3 (-->4) is a key step in the first total synthesis of (+)-halichlorine. A series of protections/deprotections and a macrolaconization complete the synthesis. Halichlorine selectively inhibits the expression of the cell adhesion molecule VCAM-1. TBS=tert-butyldimethylsilyl.
94 citations