From phenylaziridine to phenylkainoids. A formal synthesis of (+/-)-phenylkainic acid.

Authors
Schneider, MR Klotz, P Ungureanu, I Mann, A Wermuth, CG
Citation
Mr. Schneider et al., From phenylaziridine to phenylkainoids. A formal synthesis of (+/-)-phenylkainic acid., TETRAHEDR L, 40(20), 1999, pp. 3873-3876
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
20
Year of publication
1999
Pages
3873 - 3876
Database
ISI
SICI code
0040-4039(19990514)40:20<3873:FPTPAF>2.0.ZU;2-3
Abstract
The condensation of phenylaziridines (3a/3b) with 3-cyclopentenylsilane (4) in presence of BF3.Et2O yielded amino-cyclopentenyl adducts (5a-8a) and (5 b-8b). Heterocyclisation of the omega-amino-olefins assisted by Pd(OAc)(2) afforded the azabicyclo adducts 2a/2'a and 2b/2'b. Oxidation of the interna l double bond, followed by epimerization at C(2) was realized by KH in pres ence of 18-crown-6 yielding 11, the fully protected phenylkainic acid. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.