Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis.
Angew Chem Int Ed Engl
; 60(16): 8874-8881, 2021 04 12.
Article
em En
| MEDLINE
| ID: mdl-33533120
ABSTRACT
Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael-Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsinsâ
A, B, and D and plakorsinâ
D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.
Palavras-chave
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Compostos Organometálicos
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Paládio
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Fosfinas
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Produtos Biológicos
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Furanos
Tipo de estudo:
Risk_factors_studies
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article