Helvetica Chimica Acta p. 1706 - 1710 (1980)
Update date:2022-08-16
Topics:
Oppolzer, Wolfgang
Grayson, J. Ian
The racemic alkaloids chanoclavine I (1) and isochanoclavine I (2) have been synthesized stereoselectively from indole-4-carbaldehyde (3) by a sequence of 11 operations in overall yields of 14percent and 2.4percent, respectively.The key step 6->8 (Scheme 2) involves a transient nitrone 7 which undergoes a regio- and stereoselective intramolecular cycloaddition to a 1,2-disubstituted olefinic bond.
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