Enantioselective Total Synthesis of (+)-Hinckdentine A via a Catalytic Dearomatization Approach.
J Am Chem Soc
; 138(44): 14578-14581, 2016 11 09.
Article
em En
| MEDLINE
| ID: mdl-27771949
ABSTRACT
Optically pure hinckdentine A was synthesized on a 300 mg scale via an asymmetric catalysis-based strategy. The key steps to the first asymmetric synthesis involved (i) enantioselective dearomative cyclization of an achiral N-acyl indole that allowed for the efficient construction of the key polycyclic indoline intermediate with a crucial tetrasubstituted stereogenic carbon center, (ii) Beckmann fragmentation-mediated ring expansion, (iii) rearrangement-based introduction of an anilinic nitrogen atom, (iv) regioselective tribromination, and (v) final closure of the cyclic amidine moiety.
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Base de dados:
MEDLINE
Assunto principal:
Quinazolinas
Idioma:
En
Ano de publicação:
2016
Tipo de documento:
Article