Photochemical cycloaddition of mono-, 1,1-, and 1,2-disubstituted olefins to a chiral 2(5H)-furanone. Diastereoselective synthesis of (+)-lineatin.
The photochemical [2 + 2] cycloaddition of (S)-4-methyl-5-O-pivaloyloxymethyl-2(5H)-furanone, 5, to vinyl acetate, vinyl pivalate, tert-butyl vinyl ether, 1,1-diethoxyethylene, and (Z)- and (E)-1,2-dichloroethylene has been studied. A practical synthesis of (+)-lineatin from 5 has been developed via the functionalized cyclobutane 6.
Racamonde
Marta
M
Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
Alibés
Ramon
R
Figueredo
Marta
M
Font
Josep
J
de March
Pedro
P
D000475:Alkenes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry; D010777:Photochemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D005663:Furans; D010675:Pheromones; D011714:Pyrans; C037523:lineatin