Literature DB >> 18781804

Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide.

Gisela G Bardají1, Mariona Cantó, Ramón Alibés, Pau Bayón, Félix Busqué, Pedro de March, Marta Figueredo, Josep Font.   

Abstract

A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide.

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Year:  2008        PMID： 18781804     DOI： 10.1021/jo801470u

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  An Enantioselective Approach to the Securinega Alkaloids: The Total Synthesis of (+)-Norsecurinine and (+)-Allonorsecurinine.

Authors:  Matthew R Medeiros; John L Wood
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

2.  Enantiocontrolled Preparation of ϒ-Substituted Cyclohexenones: Synthesis and Kinase Activity Assays of Cyclopropyl-Fused Cyclohexane Nucleosides.

Authors:  Sergio Jurado; Beatriz Domínguez-Pérez; Ona Illa; Jan Balzarini; Félix Busqué; Ramon Alibés
Journal:  Int J Mol Sci       Date:  2022-08-26       Impact factor: 6.208

3.  Collective total synthesis of C4-oxygenated securinine-type alkaloids via stereocontrolled diversifications on the piperidine core.

Authors:  Sangbin Park; Gyumin Kang; Chansu Kim; Dongwook Kim; Sunkyu Han
Journal:  Nat Commun       Date:  2022-09-02       Impact factor: 17.694
  3 in total

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