Total Synthesis of Sarpagine-Related Bioactive Indole Alkaloids.
Chemistry
; 24(10): 2354-2359, 2018 Feb 16.
Article
em En
| MEDLINE
| ID: mdl-29244896
ABSTRACT
Extension of the asymmetric Pictet-Spengler reaction to bulkier Nb -alkylated tryptophan derivatives resulted in an improved stereospecific access to the key bicyclo[3.3.1]nonane core of bioactive C-19 methyl substituted sarpagine/macroline/ajmaline indole alkaloids with excellent diastereoselectivity by internal asymmetric induction. Complete stereocontrol of the C-19 methyl function in either the α- or ß-configuration was achieved, which enables the total synthesis of any member from this group of thirty alkaloids. We report herein, the total synthesis of macrocarpines (A-C) 1-3, talcarpine 4, N(4)-methyl-N(4),21-secotalpinine 5, dihydroperaksineâ
8 and deoxyperaksineâ
9.
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Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Triptofano
/
Alcaloides Indólicos
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article