Total syntheses of (+/-)-cherylline and (+/-)-latifine

Authors
Couture, A Deniau, E Lebrun, S Grandclaudon, P
Citation
A. Couture et al., Total syntheses of (+/-)-cherylline and (+/-)-latifine, J CHEM S P1, (7), 1999, pp. 789-794
Citations number
41
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
7
Year of publication
1999
Pages
789 - 794
Database
ISI
SICI code
0300-922X(19990407):7<789:TSO(A(>2.0.ZU;2-#
Abstract
A new total synthesis of the two phenolic alkaloids (+/-)-cherylline 1 and (+/-)-latifine 2 isolated from Crinum species is described. The two key ste ps in the elaboration of these natural products are an anionic variant of t he Fries rearrangement which gives access to the congested o-aroylbenzoic a cid derivatives 26 and 27, and an intramolecular Horner reaction involving the corresponding N-phosphorylmethylbenzamide derivatives 8 and 9.