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Issue 32, 2012
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Total synthesis and structural elucidation of ent-micropyrone and (+)-ascosalipyrone

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Abstract

The total synthesis of 6-[(1S,3S)-1,3-dimethyl-2-oxopentyl]-4-hydroxy-3,5-dimethyl-2H-pyran-2-one (22), the enantiomer of the natural product micropyrone (1), was achieved in 9 linear steps (10% overall yield), from Evans auxiliary (R)-12 with key coupling of the dianion of dione 17 and aldehyde 11. Formation of the pyrone ring and subsequent oxidation at C7 was achieved without epimerization of the sensitive position α to both the pyrone ring and the carbonyl. The same sequence using the alternate dione 24 achieved the total synthesis of 6-[(1S,3S)-1,3-dimethyl-2-oxopentyl]-4-hydroxy-3-methyl-2H-pyran-2-one (28), the (+)-enantiomer of the natural product, ascosalipyrone (2). In both cases diastereomeric aldehydes 11 and 16 were taken through the synthetic sequence to give two possible diastereomers of the natural products. Comparison of the 1H and 13C NMR data for the synthetic isomers with that reported for the natural products determined their relative stereochemistry. Comparison of the optical rotation obtained for 22 established it to be the enantiomer of micropyrone.

Graphical abstract: Total synthesis and structural elucidation of ent-micropyrone and (+)-ascosalipyrone

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Publication details

The article was received on 08 Mar 2012, accepted on 12 Jun 2012 and first published on 13 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25501D
Citation: Org. Biomol. Chem., 2012,10, 6547-6553
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    Total synthesis and structural elucidation of ent-micropyrone and (+)-ascosalipyrone

    C. Gregg and M. V. Perkins, Org. Biomol. Chem., 2012, 10, 6547
    DOI: 10.1039/C2OB25501D

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