The first total synthesis of phomopsolidone A

[Display omitted] •First stereoselective total synthesis of a 5-substituted γ-lactone, phomopsolidone A has been achieved.•This was identified from the fungus Phomopsis sp. of Grapevine plants with esca symptoms in Ticino, Switzerland.•Cost-effective (S)-lactaldehyde and l-(+)-DET were used as start...

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Bibliographic Details
Published in:Tetrahedron letters 2016-05, Vol.57 (19), p.2109-2111
Main Authors: Raju, Kasa Shiva, Raju, Atla, Sabitha, Gowravaram
Format: Article
Language:English
Subjects:
First synthesis
Grignard addition reaction
Lactonization
Still–Gennari
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Summary:[Display omitted] •First stereoselective total synthesis of a 5-substituted γ-lactone, phomopsolidone A has been achieved.•This was identified from the fungus Phomopsis sp. of Grapevine plants with esca symptoms in Ticino, Switzerland.•Cost-effective (S)-lactaldehyde and l-(+)-DET were used as starting materials.•Still–Gennari olefination and acid catalyzed one-pot lactonization reactions were utilized.•1,2-syn selective Grignard addition of alkyne to aldehyde was utilized. The first total synthesis of phomopsolidone A has been accomplished. The key features of the synthesis include the use of a stereoselective Grignard addition reaction, Still–Gennari and acid catalyzed lactonization reactions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.04.004