Tetrahedron p. 3695 - 3706 (1983)
Update date:2022-08-03
Topics:
Oppolzer, W.
Grayson, J. I.
Wegmann, H.
Urrea, M.
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 percent, respectively.Further syntheses of isochanoclavine I (2), paliclavine (5) and costaclavine (6), via the same isoxazolidine 18 are described.The key step 16-->18 (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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Doi:10.1016/0022-328X(83)87157-5
(1983)Doi:10.1002/hc.20142
(2005)Doi:10.1021/jo00182a037
(1984)Doi:10.1021/jo00366a012
(1986)Doi:10.1016/j.bmcl.2004.09.051
(2004)Doi:10.1002/ejoc.201500404
(2015)
