6-Exo-spiro (alkoxycarbonylamino)methyl radical cyclization: highly regio- and stereoselective synthesis of (-)-sibirine.
[reaction: see text] The (methoxycarbonylamino)methyl radical can be readily generated from its PhSe precursor and undergoes preferential 6-exo-spiro cyclization when PhSO(2) is attached at the distal alkene carbon. This property was applied to the synthesis of the racemic and optically active spirocyclic alkaloid sibirine.
Koreeda
Masato
M
Department of Chemistry, University of Michigan, Ann Arbor 48109-1055, USA. koreeda@umich.edu
Wang
Yamin
Y
Zhang
Liming
L
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D013141:Spiro Compounds; C467926:sibirine