Structural Determination of Montanacin D by Total Synthesis

Structural Determination of Montanacin D by Total Synthesis

The first total syntheses of acetogenin 3 and its 4S,8R-isomer are described. The key step involves intermolecular metathesis of an α,β-unsaturated ketone carrying a tetrahydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of n...

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Bibliographic Details
Published in:Organic letters Vol. 10; no. 19; pp. 4223 - 4226
Main Authors: Takahashi, Shunya, Hongo, Yayoi, Tsukagoshi, Yuki, Koshino, Hiroyuki
Format: Journal Article
Language:English
Published: United States American Chemical Society 02-10-2008
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
4-Butyrolactone - chemistry
Pyrans - chemical synthesis
Pyrans - chemistry
Stereoisomerism
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Summary:The first total syntheses of acetogenin 3 and its 4S,8R-isomer are described. The key step involves intermolecular metathesis of an α,β-unsaturated ketone carrying a tetrahydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801576z