A novel spiropiperidine system I i.e. an aza structural analog of histrionicotoxin was constructed from 2-cyano-6-phenyloxazolopiperidine synthon II. The suitable quaternary carbon was created by alkylation at the position alpha to the nitrile followed by transformation of the nitrile group into a primary amine. Final aminoreductive cyclization gave the spiro system. [on SciFinder (R)]
Title
Asymmetric synthesis. XX. Preparation of a novel spiropiperidine system by the CN(R,S) method
Published in
Tetrahedron Letters
Volume
30
Issue
46
Pages
6323-6
Date
1989
ISSN
0040-4039
Note
CAN 113:24298
31-4
Alkaloids
Inst. Chim. Subst. Nat.,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
127628-08-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and cyclization of, with formaldehyde); 127628-06-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and decyanation of); 127628-07-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrogenolysis of); 127708-19-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. cyclization of); 127708-18-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of, with butyllithium); 127628-05-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of); 127628-04-0P; 127628-09-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 88056-92-2 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with (bromoethyl)dioxolane); 18742-02-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with cyanophenyloxazolopiperidine)
Record creation date
2010-11-25
