Total Enantioselective Synthesis of the Endophytic Fungal Polyketide Phomolide H and Its Structural Revision | Zendy

McNulty James | Zendy; McLeod David | Zendy

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Total Enantioselective Synthesis of the Endophytic Fungal Polyketide Phomolide H and Its Structural Revision

Author(s) -

McNulty James,

McLeod David

Publication year - 2017

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201601172

Subject(s) - polyketide , enantioselective synthesis , chemistry , diastereomer , natural product , stereochemistry , total synthesis , tartaric acid , methanol , organic chemistry , biosynthesis , catalysis , enzyme , citric acid

A total synthesis of the proposed structure of the natural polyketide‐macrolactone phomolide H 2 has been achieved following a bidirectional strategy from l ‐tartaric acid. The originally assigned structure of phomolide H displayed discordant NMR spectroscopic data in comparison with synthetic 2 . The synthetic strategy was extended to prepare diastereomers and epimeric methyl‐ethers of the natural product, structural analysis of which revealed a match of the natural product with diastereomer 27 . The structural revision of phomolide H from 2 to the methanol solvate of compound 27 is presented.

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