A double alkylation—ring closing metathesis approach to spiroimines

As part of a programme directed towards the synthesis of the marine toxins, the spirolides and gymnodimine, a convenient synthesis of the key bicyclic spiroimine ring systems has been developed. The method involves double alkylation of a simple lactam, Grubbs ring closing metathesis of the resultant...

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Bibliographic Details
Published in:Tetrahedron 2004-06, Vol.60 (26), p.5613-5622
Main Authors: Brimble, Margaret A, Trzoss, Michael
Format: Article
Language:English
Subjects:
Gymnodimi
Spirolactams
β-Trimethylsilylethoxycarbonyl (TEOC)
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Summary:As part of a programme directed towards the synthesis of the marine toxins, the spirolides and gymnodimine, a convenient synthesis of the key bicyclic spiroimine ring systems has been developed. The method involves double alkylation of a simple lactam, Grubbs ring closing metathesis of the resultant dialkylated lactam then reduction of the lactam to an imine. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.04.059