Total synthesis and stereochemical determination of yoshinone A

• Published in: Phytochemistry (Oxford) Vol. 132; pp. 109 - 114
• Main Authors: Shinomiya, Seiichi, Iwasaki, Arihiro, Ohno, Osamu, Suenaga, Kiyotake
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01-12-2016
• Subjects: 3T3 Cells; Adipocytes - drug effects; Animals; Cell Differentiation; Cyanobacteria - chemistry; Leptolyngbya sp; Marine Biology; Marine cyanobacteria; Mice; Polyketide; Polyketides - chemistry; Polyketides - isolation & purification; Polyketides - pharmacology; Pyrones - chemical synthesis; Pyrones - chemistry; Pyrones - isolation & purification; Pyrones - pharmacology; Stereoisomerism; Total synthesis; Yoshinone A; Polyketide; Yoshinone A; Leptolyngbya sp; Marine cyanobacteria; Total synthesis
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2016.10.005

In 2014, the γ-pyrone-containing polyketide, yoshinone A, was isolated from the marine cyanobacterium Leptolyngbya sp. and its structure was determined. Yoshinone A inhibited differentiation of 3T3-L1 cells into adipocytes, with an EC50 value of 420 nM without any cytotoxicity, and therefore is expected to be a lead compound for obesity drugs. To establish its absolute configuration, and to provide sufficient amounts for further research, the total synthesis of yoshinone A was achieved through synthesis of its two possible diastereomers.
The absolute stereochemistry of yoshinone A, a γ-pyrone-containing polyketide isolated from the marine cyanobacterium Leptolyngbya sp., was established based on its total synthesis. [Display omitted]
•Total synthesis of yoshinone A was achieved.•The absolute configuration of yoshinone A was clarified.•A synthetic procedure to this rare natural product was established.