Highly efficient and diastereoselective synthesis of (+)-lineatin.
[reaction: see text] 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.
Alibés
Ramon
R
Departament de Química and Servei de Ressonància Magnètica Nuclear, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
de March
Pedro
P
Figueredo
Marta
M
Font
Josep
J
Racamonde
Marta
M
Parella
Teodor
T
D003500:Cyclization; D008968:Molecular Conformation; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
D010675:Pheromones; D011714:Pyrans; C037523:lineatin