Literature DB >> 12182622

Synthesis of chiral pilocarpine analogues via a C-8 ketone intermediate.

Kenneth G Holden1, Matthew N Mattson, Kyung Hoi Cha, Henry Rapoport.   

Abstract

The synthesis of a chiral pilocarpine analogue 3 in which the lactone ring is replaced by an oxazolidinone and the bridging methylene group is in the ketone oxidation state has been accomplished. The utility of this compound as a key intermediate for the preparation of more complex structures was demonstrated by its reduction to two alcohol epimers and its reaction with a methylene ylide.

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Year:  2002        PMID: 12182622     DOI: 10.1021/jo0111210

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


  3 in total

1.  Synthesis of diethynyltriptycene-linked dipyridyl ligands.

Authors:  Jeremy J Kodanko; Anna J Morys; Stephen J Lippard
Journal:  Org Lett       Date:  2005-10-13       Impact factor: 6.005

2.  Tetrahydropyranyl: A Non-aromatic, Mild-Acid-Labile Group for Hydroxyl Protection in Solid-Phase Peptide Synthesis.

Authors:  Anamika Sharma; Iván Ramos-Tomillero; Ayman El-Faham; Hortensia Rodríguez; Beatriz G de la Torre; Fernando Albericio
Journal:  ChemistryOpen       Date:  2017-03-08       Impact factor: 2.911

Review 3.  Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry.

Authors:  Anamika Sharma; Iván Ramos-Tomillero; Ayman El-Faham; Ernesto Nicolas; Hortensia Rodriguez; Beatriz G de la Torre; Fernando Albericio
Journal:  ChemistryOpen       Date:  2017-03-08       Impact factor: 2.911

  3 in total

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