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Scientific article
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Total syntheses of clavine alkaloids by an intramolecular nitrone-olefin cycloaddition reaction

Published inTetrahedron, vol. 39, no. 22, p. 3695-3705
Publication date1983
Abstract

The racemic ergot alkaloids chanoclavine I (1) and 6,7-secoagroclavine (4) have been synthesized stereoselectively from indole-4-carboxaldehyde (7) in overall yields of 14 and 13%, respectively. Further syntheses of isochanoclavine I (2), paliclavine (5) and costaclavine (6), via the same isoxazolidine 18 are described. The key step 1618 (Scheme 4) involves a transient nitrone 17 which undergoes a kinetically controlled, regio- and stereoselective intramolecular cycloaddition to a 1,2-disubstituted olefinic bond.

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Citation (ISO format)
VON OPPOLZER, Wolfgang et al. Total syntheses of clavine alkaloids by an intramolecular nitrone-olefin cycloaddition reaction. In: Tetrahedron, 1983, vol. 39, n° 22, p. 3695–3705. doi: 10.1016/S0040-4020(01)88608-7
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ISSN of the journal0040-4020
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