Topic
Intramolecular reaction
About: Intramolecular reaction is a research topic. Over the lifetime, 5015 publications have been published within this topic receiving 138213 citations.
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TL;DR: Two new polyhydroxylated nortropane analogues closely related with Calystegines have been prepared in excellent chemical yields and complete selectivity through the recently confirmed thermally induced 2-aza-Cope rearrangement of nitrones.
Abstract: Two new polyhydroxylated nortropane analogues closely related with Calystegines have been prepared in excellent chemical yields and complete selectivity. A synthetic strategy based on consecutive nucleophilic allylation, oxidation, and intramolecular dipolar cycloaddition was developed. The formation of key intermediate cycloadducts were observed to take place through the recently confirmed thermally induceded 2-aza-Cope rearrangement of nitrones.
44 citations
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TL;DR: In this paper, the decacyclic ciguatoxin model 2, which contains the F−M ring framework of the natural product, has been achieved through the assembly of pentacycic oxonane 4 and JKLM ring fragment 5.
Abstract: A highly convergent synthesis of the decacyclic ciguatoxin model 2, which contains the F−M ring framework of the natural product, has been achieved through the assembly of pentacyclic oxonane 4 and JKLM ring fragment 5. The two key steps in the synthesis of the former compound are (i) a Lewis acid-mediated intramolecular reaction of a γ-alkoxyallylsilane with an acetal group to form an O-linked oxacycle and (ii) a SmI2-mediated intramolecular Reformatsky reaction leading to construction of the annelated oxonane ring system. Preliminary biological investigations revealed that model compound 2 did not inhibit the binding of tritium-labeled dihydrobrevetoxin B to voltage-sensitive sodium channels at micromolar concentrations.
44 citations
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TL;DR: In this article, a new enantiospecifc route to kainic acid was established starting with (R)-4-benzyloxy-1-butyn-3-ol by employing the intramolecular Pauson-Khand reaction as the key step.
Abstract: A new enantiospecifc route to (–)-kainic acid is established starting with (R)-4-benzyloxy-1-butyn-3-ol by employing the intramolecular Pauson-Khand reaction as the key step.
44 citations
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TL;DR: In this paper, a cyclization of the latter with SeCl 4 gave 6-X-4,5,7- trifluoro-2,1,3-benzoselenadiazoles whose reduction led to the corresponding 1,2-diamino- benzenes.
44 citations
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TL;DR: In this paper, a ring closure of functionalized 2-trifluoromethyl-1-alkenes was used to construct fluorocarbon-bearing cyclic systems.
Abstract: Fluorine-containing heterocyclic and carbocyclic compounds attract widespread attention as important components of agrochemicals, pharmaceuticals, materials, and catalysts. To provide a general route to these compounds, we have developed a new methodology to construct fluorocarbon-bearing cyclic systems based on ring closure of functionalized 2-trifluoromethyl-1-alkenes, readily obtained from commercially available CH2=C(CF3)Br or CF3CO2Et. Their intramolecular reactions, such as nucleophilic substitution or addition, alkene insertion, and electrocyclization, provide a wide variety of five- and six-membered heterocycles and carbocycles bearing a fluorinated one-carbon unit (a =CF2, CHF2, or CF3 group). To construct five-membered rings, we successfully accomplished a nucleophilic 5-endo-trig cyclization and 5-endo alkene insertion, normally disfavored processes, as well as fluorine-directed Nazarov cyclization.
44 citations