203244-99-9Relevant academic research and scientific papers
A study of vinyl radical cyclization using N-alkenyl-7-bromo-substituted hexahydroindolinones
Padwa, Albert,Rashatasakhon, Paitoon,Ozdemir, Ayse Daut,Willis, Jerremey
, p. 519 - 528 (2007/10/03)
(Chemical Equation Presented) A new method for the synthesis of the octahydropyrrolo[3,2,1-ij]quinoline ring system that possesses the characteristic skeleton of the aspidosperma family of alkaloids has been developed. The method utilizes an intramolecula
Six- versus five-membered ring formation in radical cyclizations of 7-bromo-substituted hexahydroindolinones
Rashatasakhon, Paitoon,Ozdemir, Ayse Daut,Willis, Jerremey,Padwa, Albert
, p. 917 - 920 (2007/10/03)
(Equation presented) Radical cyclization of N-allyl-7-bromo-3a-methyl- hexahydroindol-2-one affords a six-membered ring product that prevails over the isomeric five-membered compound. The former product is generated through two reaction pathways: (a) 6-en
β- and γ-lactams by nickel powder mediated 4-exo or 5-endo radical cyclisations. A concise construction of the mesembrine skeleton
Cassayre, Jerome,Quiclet-Sire, Beatrice,Saunier, Jean-Baptiste,Zard, Samir Z.
, p. 1029 - 1040 (2007/10/03)
N-Alkenyl trichloroacetamides, upon treatment with nickel powder and acetic acid in refluxing 2-propanol undergo reversible 4-exo radical cyclisation. The cyclised radical can be trapped in different ways leading to β-lactams. When the trap is omitted or not efficient enough, unusual irreversible 5-endo cyclisation occurs affording functionalised five-membered lactams. Synthesis of bicyclic γ-lactams has also been examined providing in few steps an access to the Sceletium alkaloids skeleton.
