Enantioselective synthesis of (+)-polyzonimine, defensive monoterpene alkaloid produced by a milliped Polyzonium rosalbum, and determination of its S absolute configuration by Its conversion to (4S,5R,6S)-(+)-nitropolyzonamine
AUTOR(ES)
Takagi, Yasuyo, Mori, Kenji
FONTE
Journal of the Brazilian Chemical Society
DATA DE PUBLICAÇÃO
2000-12
RESUMO
A adição de Michael da enamina derivada do 2,2-dimetilciclopentanocarboxaldeído e do éter metílico do (S)-prolinol com o nitroetileno, forneceu o aduto correspondente em 75-76% ee, o qual foi convertido na (+)-polizonimina enantiomericamente pura, um espiro composto nitrogenado isolado das glândulas que contêm os compostos de defesa do "milliped" Polyzonium rosalbum. Através da conversão da (+)-polizonimina na (4S, 5R, 6S)-(+)-nitropolizonamina, foi possível estabelecer a configuração absoluta desta como sendo S.
Documentos Relacionados
- Spider sedation induced by defensive chemicals of milliped prey*
- Enantioselective synthesis of (R)-isocarvone from (S)-perillaldehyde
- Enantioselective synthesis of (R)-isocarvone from (S)-perillaldehyde
- Enantioselective synthesis of both (-)-(R)-and (+)-(S)-angustureine controlled by enzymatic resolution
- The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone