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 t...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-02, Vol.68 (4), p.1216-1224
Main Authors: Yamashita, Masayuki, Ohta, Nobukazu, Shimizu, Takashi, Matsumoto, Kayoko, Matsuura, Yoko, Kawasaki, Ikuo, Tanaka, Tetsuaki, Maezaki, Naoyoshi, Ohta, Shunsaku
Format: Article
Language:English
Subjects:
Benzofurans - analysis
Benzofurans - chemical synthesis
Benzofurans - pharmacology
Cells, Cultured - drug effects
Chemistry
Crystallography, X-Ray
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lindera - chemistry
Melanins - biosynthesis
Melanoma, Experimental - metabolism
Molecular Structure
Organic chemistry
Plants, Medicinal - chemistry
Preparations and properties
Stereoisomerism
Tumor Cells, Cultured
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo020619e