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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 total synthesis of the antivirally active glycolipid cycloviracin B(1) (1) is described, showing that the entire construct is necessary for appreciable and selective antiviral activity.
Abstract: The first total synthesis of the antivirally active glycolipid cycloviracin B1 (1) is described. The approach is based on a two-directional synthesis strategy which constructs the C2-symmetrical macrodiolide core of the target by an efficient template-directed macrodilactonization reaction promoted by 2-chloro-1,3-dimethylimidazolinium chloride 14 as the activating agent. Attachment of the lateral fatty acid chains to the lactide core thus formed features not only one of the most advanced ligand-controlled addition reactions of a functionalized dialkyl zinc reagent to a polyfunctional aldehyde, but also a highly demanding Julia−Kocienski olefination of a tetrazolyl sulfone bearing electrophilic and base-labile β-hydroxy ester motifs. By virtue of the flexibility of this synthesis plan, it was possible to prepare a series of macrodiolide cores differing only in the absolute stereochemistry at the branching points as well as a host of model compounds for the fatty acid appendices of cycloviracin. Comparison...
96 citations
TL;DR: An X-ray structure of N-MOM-rhazinal, which provides insight into the conformation of the strained 9-membered lactam ring, is described.
Abstract: A concise synthesis of (±)-rhazinal that hinges on novel oxidative Heck cyclizations and palladium-catalyzed direct couplings is described. An X-ray structure of N-MOM-rhazinal, which provides insight into the conformation of the strained 9-membered lactam ring, is described.
96 citations
TL;DR: In this paper, the asymmetric synthesis of (+)-dictamnol is described, based on the rhodium catalyzed [5.3.2] cycloaddition of an allene and vinylcyclopropane.
96 citations
TL;DR: A direct ruthenium-catalyzed radical chloroalkylation of N-acyl oxazolidinones capitalizing on valence tautomerism of titanium enolates has been developed.
Abstract: A direct ruthenium-catalyzed radical chloroalkylation of N-acyl oxazolidinones capitalizing on valence tautomerism of titanium enolates has been developed. The chloroalkylation method served as the centerpiece in the enantioselective total synthesis of trichloroleucine-derived marine natural product neodysidenin.
96 citations
TL;DR: The total synthesis of coleophomone B (2), C (3), and D (4) confirmed that it exists as a dynamic mixture of isomeric forms with a different aromatic substitution pattern from the other family members.
Abstract: Members of the coleophomone family of natural products all possess several intriguing and challenging architectural features, as well as exhibit unusual biological activity. They, therefore, constitute attractive targets for synthesis. In this Article, we describe the total synthesis of coleophomones B (2), C (3), and D (4). The highly strained and congested 11-membered macrocycle of coleophomones B (2) and C (3) was constructed using an impressive olefin metathesis reaction. Furthermore, both of the requisite geometric isomers of the Delta(16,17) within the macrocycle could be accessed from a common precursor, facilitating a divergence that lent the coleophomone B (2)/C (3) synthesis an unusually high degree of efficiency. The synthesis of coleophomone D (4) confirmed that it exists as a dynamic mixture of isomeric forms with a different aromatic substitution pattern from the other family members.
96 citations