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

Article Article scientifique Article Total syntheses of clavine alkaloids by an intramolecular nitrone-olefin cycloaddition reaction eng 1983 author Von Oppolzer Wolfgang 25270 author Grayson James Ian 66071 author Wegmann Helmut 72958 author Urrea Miguel Angel 72701 3695-3705 10.1016/S0040-4020(01)88608-7 0040-4020 https://linkinghub.elsevier.com/retrieve/pii/S0040402001886087 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 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. Dewey 540 36 Département de chimie organique 141 false Tetrahedron 39 22 a8122c92-f6b5-4bc5-9afe-7279adb7749b Article (Published version) Restricted Oppolzer_T_1983393695.pdf 7609499 application/pdf d4195c9e6a176a548a86849bb692ddd5928243e331ef0bbc44091e35881868dd restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Total syntheses of clavine alkaloids by an intramolecular nitrone-olefin cycloaddition reaction	Tetrahedron			1983	72	0

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Urrea, Miguel Angel