Highly Efficient and Diastereoselective Synthesis of (+)-Lineatin

A linear sequence was used to synthesize (+)-lineatin in 14 steps and 14% overall yield from a homochiral 2(5H)-furanone. Key steps of this synthetic approach feature the diastereoselective construction of a cyclobutene through a photochemical [2 + 2] cycloaddition and a regiocontrolled oxymercurati...

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Bibliographic Details
Published in:Organic letters 2004-04, Vol.6 (9), p.1449-1452
Main Authors: Alibés, Ramon, de March, Pedro, Figueredo, Marta, Font, Josep, Racamonde, Marta, Parella, Teodor
Format: Article
Language:English
Subjects:
Cyclization
Molecular Conformation
Pheromones - chemical synthesis
Pheromones - chemistry
Pyrans - chemical synthesis
Pyrans - chemistry
Sensitivity and Specificity
Stereoisomerism
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Summary:A linear sequence was used to synthesize (+)-lineatin in 14 steps and 14% overall yield from a homochiral 2(5H)-furanone. Key steps of this synthetic approach feature the diastereoselective construction of a cyclobutene through a photochemical [2 + 2] cycloaddition and a regiocontrolled oxymercuration reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0497032