Synthesis and X-ray analysis of an unprecedented and stable 2-aza-4,4-spirocyclopropacyclohexadienone.
Org Lett
; 5(14): 2577-9, 2003 Jul 10.
Article
en En
| MEDLINE
| ID: mdl-12841785
ABSTRACT
[structure see text] An efficient eight-step synthesis (54% overall) and the subsequent X-ray characterization of 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]-3-azaindol-4-one (CBA) containing an aza variant of the CC-1065/duocarmycin alkylation subunit are detailed. Despite the unique deep-seated aza modification providing an unprecedented and stable 2-aza-4,4-spirocyclopropacyclohexadienone, CBA proved to be structurally identical with CBI, the carbon analogue, in terms of the stereoelectronic alignment of the key cyclopropane, its bond lengths, and the length of the diagnostic C3a-N2 bond reflecting the extent of vinylogous amide conjugation.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Compuestos de Espiro
/
Ciclohexanos
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2003
Tipo del documento:
Article
País de afiliación:
Estados Unidos