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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: An efficient synthesis of the antitumor alkaloid (+/-)-strychnofoline is documented and the ability to conduct annulation reactions of spirocyclopropyloxindoles with functionalized cyclic imines provides new avenues for the preparation of this important class of biologically active structures.
Abstract: An efficient synthesis of the antitumor alkaloid (±)-strychnofoline is documented. Key to the development of the highly convergent strategy delineated is the coupling of a cyclic imine with spiro[cyclopropan-1,3‘-oxindole], which takes place in a highly diastereoselective manner. The ability to conduct annulation reactions of spirocyclopropyloxindoles with functionalized cyclic imines provides new avenues for the preparation of this important class of biologically active structures.
135 citations
TL;DR: It is demonstrated that an acyclic, chiral η(3)-allylpalladium fragment generated in a catalytic asymmetric Heck cyclization can be trapped by even a weakly nucleophilic diketopiperazine more rapidly than it undergoes diastereomeric equilibration.
Abstract: A catalytic intramolecular Heck reaction, followed by capture of the resulting η(3)-allylpalladium intermediate by a tethered diketopiperazine, is the central step in a concise synthetic route to (-)-spirotryprostatin B and three stereoisomers. This study demonstrates that an acyclic, chiral η(3)-allylpalladium fragment generated in a catalytic asymmetric Heck cyclization can be trapped by even a weakly nucleophilic diketopiperazine more rapidly than it undergoes diastereomeric equilibration.
135 citations
135 citations
TL;DR: The preparation of the diastereomerically pure beta-tetralone ketal 4 is reported and the key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20.
Abstract: The preparation of the diastereomerically pure beta-tetralone ketal 4 is reported. Intramolecular alkylidene C-H insertion followed by hydrolysis of 4 proceeded to give the enantiomerically pure cyclopentene 15. The key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20. Enone 20 was converted over several steps to (-)-morphine 1.
135 citations
TL;DR: An efficient total synthesis of (+)-preussin, (25,3S,SR)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol (1), was achieved by way of a convergent, intramolecular imidotitanium-alkyne [2+2] cycloaddition-acyl cyanide condensation sequence as discussed by the authors.
Abstract: An efficient stereoselective total synthesis of (+)-preussin, (25,3S,SR)-1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol (1), was achieved by way of a convergent, intramolecular imidotitanium-alkyne [2+2] cycloaddition-acyl cyanide condensation sequence
134 citations