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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: Eight concise steps suffice for the first total synthesis of the title compound 1, which inhibits the transitions from the G2 and M phases into the next phases of the cell cycle.
Abstract: Eight concise steps suffice for the first total synthesis of the title compound 1, which inhibits the transitions from the G2 and M phases into the next phases of the cell cycle. Key steps in the synthesis are a stereocontrolled oxidative rearrangement of an indole to form the chiral spiroindolinone nucleus and a regioselecitve sulfoxide elimination.
94 citations
TL;DR: Intramolecular cycloaddition reactions are central in the total syntheses of colombiasin A and elisapterosin B described, which use (?)-dihydrocarvone as the starting material.
Abstract: Intramolecular cycloaddition reactions are central in the total syntheses of colombiasin A (1) and elisapterosin B (2) described, which use (?)-dihydrocarvone as the starting material. A Moore rearrangement of a vinylcyclobutene is used to initiate the cycloaddition.
94 citations
94 citations
TL;DR: In this article, the stereocontrolled total synthesis of gelsemine via 21-oxogelsemine was reported, which features a stereoselective condensation of cyclopropyl carboxaldehyde 11 and 4-iodo-oxindole, a facile construction of the bicyclo(3.2.1) intermediate with complete control of the stereochemistry by means of a novel application of divinylcyclopropane-cycloheptadiene rearrangement, and an unprecedented silver ion-mediated lactam formation between carbamoyl chloride
Abstract: The stereocontrolled total synthesis of gelsemine (1) via 21-oxogelsemine (2) is reported. Our total synthesis features a stereoselective condensation of cyclopropyl carboxaldehyde 11 and 4-iodo-oxindole, a facile construction of the bicyclo(3.2.1) intermediate 20 with a complete control of the stereochemistry by means of a novel application of divinylcyclopropane-cycloheptadiene rearrangement, and an unprecedented silver ion-mediated lactam formation between carbamoyl chloride and enecarbamate.
94 citations
TL;DR: The absolute stereochemistry of the natural product is demonstrated to be opposite of that reported previously, and significant quantities of both enantiomers of this microtubule-stabilizing natural product and related structures are now available via this approach.
Abstract: An efficient biomimetic synthesis of the reported structure of the hexacyclic, cytotoxic secondary metabolite FR182877 is described. The successful route features the synthesis of a 19-membered ring carbocycle using two pi-allyl palladium(II)-mediated C-C bond-forming reactions. This polyunsaturated macrocycle undergoes tandem transannular Diels-Alder reactions that create five rings and seven stereogenic centers in one operation under mild conditions, representing the first double transannular Diels-Alder reaction. The absolute stereochemistry of the natural product is demonstrated to be opposite of that reported previously. Significant quantities of both enantiomers of this microtubule-stabilizing natural product and related structures are now available via this approach.
94 citations