Synthesis and Determination of Absolute Configuration of α‑Pyrones Isolated from Penicillium corylophilum

The first total synthesis of (S)-6-(2,9-dihydroxy­nonyl)-4-hydroxy-3-methyl-2H-pyran-2-one, 4-hydroxy-3-methyl-6-((2S,4R)-2,4,11-trihydroxy­undecyl)-2H-pyran-2-one, and its unnatural 2R,4R-isomer starting from commercially available 1,8-octanediol is described. The synthesis led to the revision of t...

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Published inJournal of organic chemistry Vol. 79; no. 22; pp. 10762 - 10771
Main Authors Yadav, J. S, Ganganna, B, Dutta, Palash, Singarapu, Kiran K
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.11.2014
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Biological Products - chemistry
Chemistry
Chemistry, Organic
Cyclization
Molecular Structure
Penicillium - chemistry
Physical Sciences
Pyrones - chemical synthesis
Pyrones - chemistry
Pyrones - isolation & purification
Science & Technology
Stereoisomerism
STEREOCHEMICAL ASSIGNMENT
STEREOSELECTIVE TOTAL-SYNTHESIS
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Summary:The first total synthesis of (S)-6-(2,9-dihydroxy­nonyl)-4-hydroxy-3-methyl-2H-pyran-2-one, 4-hydroxy-3-methyl-6-((2S,4R)-2,4,11-trihydroxy­undecyl)-2H-pyran-2-one, and its unnatural 2R,4R-isomer starting from commercially available 1,8-octanediol is described. The synthesis led to the revision of the proposed structural assignment of the natural product as (R)-6-(2,9-dihydroxy­nonyl)-4-hydroxy-3-methyl-2H-pyran-2-one. The key steps include chiral auxiliary mediated asymmetric acetate aldol reaction, dianion addition, and base mediated cyclization to form an α-pyrone ring.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo5015382