Synthesis of the fungus metabolite cladosin C

Synthesis of the fungus metabolite cladosin C

Cladosin C is one of the few known enaminotetramic acids, isolated from extracts of the deep sea fungus Cladosporium sphaerospermum. It was synthesised in ten steps and 14% overall yield by a late-stage amination of the corresponding 3-acyltetramic acid. This was obtained by a Dieckmann condensation...

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Bibliographic Details
Published in:Organic & biomolecular chemistry Vol. 15; no. 36; p. 7672
Main Authors: Linder, David, Schobert, Rainer
Format: Journal Article
Language:English
Published: England 20-09-2017
Subjects:
Cladosporium - chemistry
Cladosporium - metabolism
Molecular Structure
Polyketides - chemical synthesis
Polyketides - chemistry
Polyketides - metabolism
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Summary:Cladosin C is one of the few known enaminotetramic acids, isolated from extracts of the deep sea fungus Cladosporium sphaerospermum. It was synthesised in ten steps and 14% overall yield by a late-stage amination of the corresponding 3-acyltetramic acid. This was obtained by a Dieckmann condensation of an N-β-ketoacylaminoester derived from dehydrovalinate and the thioester-terminated side chain containing the stereogenic centre which stemmed from poly-(R)-3-hydroxybutyrate.
ISSN:1477-0539
DOI:10.1039/c7ob01795b