183867-13-2Relevant articles and documents
Ring closing metathesis in organic synthesis: Evolution of a high speed, solid phase method for the preparation of β-turn mimetics
Piscopio, Anthony D.,Miller, John F.,Koch, Kevin
, p. 8189 - 8198 (1999)
Complimentary solid phase syntheses of the Freidinger lactam class of β-turn mimetics have been developed using ring closing metathesis as both the key carbon-carbon bond forming step and the cyclative cleavage mechanism. Solid phase variants of the Fukuyama-Mitsunobu process were utilized as part of a rapid three-step sequence to construct immobilized lactam precursors. An alternative solid phase process is offered which utilizes an Ugi/ring closing metathesis reaction tandem to deliver the desired compounds in two synthetic operations.
A second generation solid phase approach to Freidinger lactams: Application of Fukuyama's amine synthesis and cyclative release via ring closing metathesis
Piscopio, Anthony D.,Miller, John F.,Koch, Kevin
, p. 2667 - 2670 (1998)
A high-speed solid phase synthesis of Freidinger lactams was accomplished using a novel variant of Fukuyama's amine synthesis and ring closing metathesis-promoted cyclative cleavage as key steps.
Synthesis of fused 3-aminoazepinones via trapping of a new class of cyclic seven-membered allenamides with furan
Schurgers, Ben,Brigou, Ben,Urbanczyk-Lipkowska, Zofia,Tourwe, Dirk,Ballet, Steven,De Proft, Frank,Van Lommen, Guy,Verniest, Guido
, p. 3712 - 3715 (2014/08/05)
Novel tricyclic tetrahydroazepinones were synthesized via an in situ Diels-Alder reaction of furan with cyclic allenamides. These reactive intermediates are the first examples of cyclic seven-membered allenamides and were prepared starting from N-(2-chlor
Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease
Zaman, Shazia,Campaner, Pietro,Abell, Andrew D.
, p. 8323 - 8331 (2008/02/04)
A versatile synthesis of hydroxylated and epoxy 1-azepin 2-ones substituted at N1, C-3 and C-4 or C-7 has been developed. The sequence involves ring-closing metathesis of an amino acid derived diene amide, followed by either epoxidation or dihydroxylation
Solid phase ring-closing metathesis: Cyclization/cleavage approach towards a seven membered cycloolefin
Van Maarseveen, Jan H.,Den Hartog, Jack A.J.,Engelen, Victor,Finner, Emil,Visser, Geb,Kruse, Chris G.
, p. 8249 - 8252 (2007/10/03)
The application of solid phase ring-closing metathesis (RCM) in a cyclization/cleavage strategy was demonstrated for the first time by the successful synthesis of the seven membered cycloolefin 4. Probably due to intermolecular metathetical dimerizations at the resin, 4 could not be obtained in higher yields than 54%.
