The asymmetric synthesis of new tetrahydropyrrolo[2,3-b]indole 19 and tetrahydropyrano[2,3-b]indole 20 rings, substituted in position C-3a and C-4a with a hydroxy- and an amino functionalized chain, respectively, was performed starting from the racemic spiro[cyclohexane-1,3'-indoline]-2',4-diones 7. The enantiopure spiro oxo-azepinoindolinone (+)-10, obtained from (+/-)-7 by the way of an asymmetric ring enlargement, and the amino acid (+)-14, obtained by the hydrolysis of 10, were prepared as key intermediates for the synthesis of enantiopure compounds ( )-19 and ( )-20. Since the amino acid 14 is the common intermediate for the chemoselective preparation of derivatives 19 and 20, experimental and computational Studies were performed in order to selectively obtain these Compounds and to provide a mechanistic rationalization for their formation.
Chemoselective asymmetric synthesis of C-3a-(3-hydroxypropyl)tetrahydropyrrolo[2,3-b]indole and C-4a-(2-aminoethyl)-tetrahydropyrano[2,3-b]indole derivatives / F. Clerici, A. Contini, M.L. Gelmi, S. Pellegrino, S. Leone, T. Pilati. - In: TETRAHEDRON. - ISSN 0040-4020. - 65:10(2009 Mar 07), pp. 1995-2004.
|Titolo:||Chemoselective asymmetric synthesis of C-3a-(3-hydroxypropyl)tetrahydropyrrolo[2,3-b]indole and C-4a-(2-aminoethyl)-tetrahydropyrano[2,3-b]indole derivatives|
CONTINI, ALESSANDRO (Secondo)
GELMI, MARIA LUISA (Corresponding)
PELLEGRINO, SARA (Primo)
LEONE, SAMANTHA (Penultimo)
|Parole Chiave:||bryozoan flustra-foliacea; marine alkaloids; claisen rearrangement; oxidative cyclization; secondary metabolites; debromoflustramine-B; cyclic tautomers; indole alkaloids; chemistry; strategy|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||7-mar-2009|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/j.tet.2009.01.004|
|Appare nelle tipologie:||01 - Articolo su periodico|