Synthesis of an azaspirane via Birch reduction alkylation prompted by suggestions from a computer program

With the aid of proposals from a computer program for synthesis design, a new method of synthesizing azaspiranes has been developed. In this method, one starts with a suitable benzoic acid ester, which is subjected to Birch reduction. Then the anionic intermediate is alkylated with 1,2-dibromoethane...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2006-09, Vol.47 (38), p.6733-6737
Main Authors: Tanaka, Akio, Kawai, Takashi, Takabatake, Tetsuhiko, Oka, Noriko, Okamoto, Hideho, Bersohn, Malcolm
Format: Article
Language:English
Subjects:
Azaspirane
Birch reduction alkylation
Heterocycles
Retrosynthesis
SYNSUP
Synthesis design
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:With the aid of proposals from a computer program for synthesis design, a new method of synthesizing azaspiranes has been developed. In this method, one starts with a suitable benzoic acid ester, which is subjected to Birch reduction. Then the anionic intermediate is alkylated with 1,2-dibromoethane. The product is subsequently reacted with an amine to give a spiro lactam.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.07.100