Abstract
The tricyclic core of martinelline and martinellic acid was rapidly assembled utilising an imino Diels-Alder reaction of an imine derived from cinnamaldehyde with a cyclic enamide. The cycloaddition was completely regioselective though the exo endo selectivity was poor. These diastercoisomers were readily separated by flash chromatography and the relative stereochemistry of the exo-isomer confirmed by single crystal X-ray crystallography. This intermediate was converted to the central core of the aforementioned alkaloids in five additional synthetic operations. (C) 2001 Elsevier Science Ltd. All rights reserved.
Original language | English |
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Pages (from-to) | 6417-6419 |
Number of pages | 3 |
Journal | Tetrahedron Letters, ISSN |
Volume | 42 |
Issue number | 36 |
Publication status | Published - 03 Sept 2001 |
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery