The synthesis of N-vanillyl-arachidonoyl-amide (arvanil) and its analogs: An improved procedure for the synthesis of the key synthon methyl 14-hydroxy-(all-cis)-5,8,11-tetradecatrienoate

Authors
Dasse, O Mahadevan, A Han, LN Martin, BR Di Marzo, V Razdan, RK
Citation
O. Dasse et al., The synthesis of N-vanillyl-arachidonoyl-amide (arvanil) and its analogs: An improved procedure for the synthesis of the key synthon methyl 14-hydroxy-(all-cis)-5,8,11-tetradecatrienoate, TETRAHEDRON, 56(47), 2000, pp. 9195-9202
Citations number
45
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
47
Year of publication
2000
Pages
9195 - 9202
Database
ISI
SICI code
0040-4020(20001117)56:47<9195:TSON(A>2.0.ZU;2-5
Abstract
Several arvanil analogs were synthesized where the end n-pentyl chain was b ranched and carried substituents at the terminal end of the chain. A high y ielding total synthesis of these analogs was developed from methyl hex-5-yn oate, which was converted to the synthon 6 in a facile five strip sequence (overall yield, 33%). The pharmacological profile of these novel analogs su ggests that they may be acting through a novel site of action for anandamid e (arachidonylethanolamide, AEA). (C) 2000 Elsevier Science Ltd. All rights reserved.