First total synthesis of (+/-)-Linderol A, a tricyclic hexahydrodibenzofuran constituent of Lindera umbellata bark, with potent inhibitory activity on melanin biosynthesis of cultured B-16 melanoma cells.
The first total synthesis of (+/-)-Linderol A, a hexahydrodibenzofuran constituent of Lindera umbellata bark, with potent inhibitory activity on the melanin biosynthesis of cultured B-16 melanoma cells, was achieved through 19 steps of reaction in 6.6% overall yield, in which the critical step was a tandem reaction of a 3-ethoxycarbonylcoumarin derivative with dimethylsulfoxonium methylide to yield the 2-ethoxycarbonylcyclopenta[b]benzofuran-3-ol derivative.
Yamashita
Masayuki
M
Kyoto Pharmaceutical University, Misasagi-Nakauchicho 5, Yamashinaku, Kyoto 607-8414, Japan.
Ohta
Nobukazu
N
Shimizu
Takashi
T
Matsumoto
Kayoko
K
Matsuura
Yoko
Y
Kawasaki
Ikuo
I
Tanaka
Tetsuaki
T
Maezaki
Naoyoshi
N
Ohta
Shunsaku
S
D001572:Benzofurans / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D002478:Cells, Cultured / Q000187:drug effects; D018360:Crystallography, X-Ray; D027443:Lindera / Q000737:chemistry*; D008543:Melanins / Q000096:biosynthesis*; D008546:Melanoma, Experimental / Q000378:metabolism; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D001572:Benzofurans; D008543:Melanins; C429131:linderol A