Chemical reactivity of phthalides. Relay synthesis of diligustilide, rel-(3'R)-3',8'-dihydrodiligustilide and wallichilide
Diels Alder reaction using Z-ligustilide (3) both as diene and dienophile afforded the natural product diligustilide (1). The relay synthesis of 5 from 1 (via situ-selective lactone ring opening, reduction with NaBH4/MeOH and lactonization with SOCl2/THF) was achieved and confirmed the revised structure of 5, a secondary constituent of Ligusticum wallichii. The natural substance wallichilide (8) was also obtained directly from 1.
Rios, Maria Yolanda,Delgado, Guillermo,Toscane, Ruben A.
p. 3355 - 3366
(2007/10/03)
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