56053-19-1Relevant academic research and scientific papers
Total Syntheses of (?)-Minovincine and (?)-Aspidofractinine through a Sequence of Cascade Reactions
Angyal, Péter,Egyed, Orsolya,Holczbauer, Tamás,Martin, Gábor,Soós, Tibor,Varga, Szilárd
supporting information, p. 13547 - 13551 (2020/06/08)
We report 8-step syntheses of (?)-minovincine and (?)-aspidofractinine using easily available and inexpensive reagents and catalyst. A key element of the strategy was the utilization of a sequence of cascade reactions to rapidly construct the penta- and hexacyclic frameworks. These cascade transformations included organocatalytic Michael-aldol condensation, a multistep anionic Michael-SN2 cascade reaction, and Mannich reaction interrupted Fischer indolization. To streamline the synthetic routes, we also investigated the deliberate use of steric effect to secure various chemo- and regioselective transformations.
Total Syntheses of Dihydroindole Aspidosperma Alkaloids: Reductive Interrupted Fischer Indolization Followed by Redox Diversification
Angyal, Péter,Egyed, Orsolya,Martin, Gábor,Soós, Tibor,Varga, Szilárd
, (2020/06/24)
We report a novel reductive interrupted Fischer indolization process for the concise assembly of the 20-oxoaspidospermidine framework. This rapid complexity generating route paves the way toward various dihydroindole Aspidosperma alkaloids with different C-5 side chain redox patterns. The end-game redox modulations were accomplished by modified Wolff-Kishner reaction and photo-Wolff rearrangement, enabling the total synthesis of (-)-aspidospermidine, (-)-limaspermidine, and (+)-17-demethoxy-N-acetylcylindrocarine and the formal total synthesis of (-)-1-acetylaspidoalbidine.
Total Synthesis of Indole Alkaloids. A New Strategy for (+/-)-19-Oxoaspidospermidine and (+/-)-19-Oxoaspidofractinine
Dufour, M.,Gramain, J.-C.,Husson, H.-P.,Sinibaldi, M.-E.,Troin, Y.
, p. 5483 - 5490 (2007/10/02)
A synthesis for the preparation of 19-oxoaspidospermidine (1) and 19-oxoaspidofractinine (2) has been developed beginning with tetracyclic amido alcohol 9.Dehydration of 9 gave enamine 10.Reduction to the corresponding enamine followed by reaction with ac
TOTAL SYNTHESIS OF (+/-) ASPIDOFRACTININE
Dufour, Monique,Gramain, Jean-Claude,Husson, Henri-Philippe,Sinibaldi, Marie-Eve,Troin, Yves
, p. 3429 - 3432 (2007/10/02)
The pentacyclic skeleton 10 of the aspidospermine group of indole alkaloids has been constructed from hexahydrocarbazol-4-one 2 with high stereoselectivity.The synthesis of (+/-) 19-oxo aspidofractinine 12, a direct precursor of aspidofractinine 4, illustrates the usefulness of this new general strategy.
APPLICATION OF THE NEW ACYLATING AGENTS TO THE SYNTHESIS OF INDOLE ALKALOIDS. A TOTAL SYNTHESIS OF (+/-)-ASPIDOFRACTININE
Kinoshita, Hitoshi,Ohnuma, Takeshi,Oishi, Takeshi,Ban, Yoshio
, p. 927 - 930 (2007/10/02)
The new acylating agents were proved to be useful for introduction of an acetyl group into the α-position of the carbonyl group by means of two-carbon Michael acceptors, which was successfully applied to
