Total syntheses of (+/-)-cryptopleurine, (+/-)-antofine and (+/-)-deoxypergularinine

Authors
Lebrun, S Couture, A Deniau, E Grandclaudon, P
Citation
S. Lebrun et al., Total syntheses of (+/-)-cryptopleurine, (+/-)-antofine and (+/-)-deoxypergularinine, TETRAHEDRON, 55(9), 1999, pp. 2659-2670
Citations number
46
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
9
Year of publication
1999
Pages
2659 - 2670
Database
ISI
SICI code
0040-4020(19990226)55:9<2659:TSO((A>2.0.ZU;2-X
Abstract
The alkaloids (+/-)-cryptopleurine 1, (+/-)-antofine 2, and (+/-)-deoxyperg ularinine 3 were synthesized by Pictet-Spengler cyclization of the 2-arylme thylpiperidine and -pyrrolidines 4, 5 and 6 obtained by sequential N-deprot ection-reduction of the parent enecarbamates 7, 8 and 9. These latter were made by the Horner reaction of phosphorylated carbamates 12 and 13 with the appropriate aldehydes 10 and 11. (C) 1999 Elsevier Science Ltd. All rights reserved.