An improved asymmetric synthesis of malyngamide U and its 2'-epimer.
J Org Chem
; 73(17): 6873-6, 2008 Sep 05.
Article
em En
| MEDLINE
| ID: mdl-18656980
ABSTRACT
An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of 1 and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.
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Base de dados:
MEDLINE
Assunto principal:
Ácidos Graxos Monoinsaturados
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Ácidos Carboxílicos
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Etanolamina
/
Cicloexanonas
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Monoterpenos
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Aldeídos
Idioma:
En
Ano de publicação:
2008
Tipo de documento:
Article