Intramolecular 1,3-dipolar cycloaddition-mediated stereoselective synthesis of disubstituted cyclopentane: a simple model for the cyclopentane ring system of polycyclic oroidine alkaloids.
Chem Asian J
; 8(1): 244-50, 2013 Jan.
Article
em En
| MEDLINE
| ID: mdl-23081863
ABSTRACT
We present a diastereoselective synthesis of disubstituted cyclopentane 8 having a nitrogen-containing quaternary carbon center, which is found in axinellamine A (5) and related compounds. During this work, we found that the 1,3-dipolar cycloaddition product 24 immediately underwent intramolecular redox reaction at the newly formed morpholin-2-one moiety, thus affording disubstituted cyclopentane containing a tertiary amine (9) stereoselectively in good yield. The amine 9 was successfully converted into guanidine 31, which corresponds to 8, through iminium cation-enamine isomerization.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Compostos Policíclicos
/
Modelos Moleculares
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Ciclopentanos
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Alcaloides
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Reação de Cicloadição
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article