Synthesis and Structural Revision of Phomopsin B, a Novel Polyketide Carrying a 10-Membered Cyclic-Ether Ring

Total synthesis of the proposed structure 2 for phomopsin B was achieved by using an intramolecular olefin metathesis as a key step. The spectral data, however, did not match with those of the natural product reported. Re-examination of the reported NMR data led to the structural revision of phomops...

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Bibliographic Details
Published in:Organic letters 2011-07, Vol.13 (13), p.3360-3363
Main Authors: Izuchi, Yuko, Koshino, Hiroyuki, Hongo, Yayoi, Kanomata, Nobuhiro, Takahashi, Shunya
Format: Article
Language:English
Subjects:
Biological Products - chemistry
Ethers, Cyclic - chemistry
Molecular Structure
Phenylacetates - chemical synthesis
Phenylacetates - chemistry
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Summary:Total synthesis of the proposed structure 2 for phomopsin B was achieved by using an intramolecular olefin metathesis as a key step. The spectral data, however, did not match with those of the natural product reported. Re-examination of the reported NMR data led to the structural revision of phomopsin B to known dothiorelone A 18. The R configuration of dothiorelone A was determined by total synthesis through a cross-metathesis with a chiral olefin 19.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2011117