Total Synthesis of the Antifungal Agent Echinocandin C

Reliably stable: A dipeptide building block with fully elaborated N‐acyl hemiaminal proved to be a versatile precursor for echinocandin C, a prototypical member of the echinocandin group of antimycotic drugs. This first total synthesis of an N‐acyl hemiaminal‐containing echinocandin is concise and h...

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Published inAngewandte Chemie (International ed.) Vol. 52; no. 22; pp. 5871 - 5875
Main Authors Messik, Frauke, Oberthür, Markus
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 27.05.2013
WILEY‐VCH Verlag
Wiley
Subjects
antifungal agents
Antifungal Agents - chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Chemistry, Pharmaceutical - methods
Curtius rearrangement
cyclopeptides
Echinocandins - chemical synthesis
Echinocandins - chemistry
Molecular Structure
N-acyl hemiaminal
Physical Sciences
Science & Technology
total synthesis
REAGENT
ANTIBIOTICS
antifungal agents
ANALOGS
IRCINIASTATIN
Curtius rearrangement
MECHANISMS
cyclopeptides
AMINO-ACIDS
RESISTANCE
CATALYTIC ASYMMETRIC DIHYDROXYLATION
total synthesis
N-acyl hemiaminal
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Summary:Reliably stable: A dipeptide building block with fully elaborated N‐acyl hemiaminal proved to be a versatile precursor for echinocandin C, a prototypical member of the echinocandin group of antimycotic drugs. This first total synthesis of an N‐acyl hemiaminal‐containing echinocandin is concise and highly convergent, thereby making additional derivatives easily accessible. PG=protecting group.
Bibliography:ArticleID:ANIE201301262
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ark:/67375/WNG-9H7TX56G-Q
DFG
Financial support by the German Science Foundation (DFG) is gratefully acknowledged. We thank Michael Marsch (Philipps-Universität Marburg) for the crystallographic analysis.
Financial support by the German Science Foundation (DFG) is gratefully acknowledged. We thank Michael Marsch (Philipps‐Universität Marburg) for the crystallographic analysis.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201301262