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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| Published in: | Organic & biomolecular chemistry Vol. 15; no. 36; p. 7672 |
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| Main Authors: | , |
| Format: | Journal Article |
| Language: | English |
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England
20-09-2017
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | Linder, David Schobert, Rainer |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28871295$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1016_j_tetlet_2017_11_023 crossref_primary_10_1021_acs_joc_0c01605 crossref_primary_10_1515_hc_2019_0015 crossref_primary_10_1039_C8NP00092A crossref_primary_10_3390_M1556 |
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| Snippet | 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... |
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| SubjectTerms | Cladosporium - chemistry Cladosporium - metabolism Molecular Structure Polyketides - chemical synthesis Polyketides - chemistry Polyketides - metabolism |
| Title | Synthesis of the fungus metabolite cladosin C |
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