Abstract |
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.
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Authors | Masayuki Yamashita, Nobukazu Ohta, Takashi Shimizu, Kayoko Matsumoto, Yoko Matsuura, Ikuo Kawasaki, Tetsuaki Tanaka, Naoyoshi Maezaki, Shunsaku Ohta |
Journal | The Journal of organic chemistry
(J Org Chem)
Vol. 68
Issue 4
Pg. 1216-24
(Feb 21 2003)
ISSN: 0022-3263 [Print] United States |
PMID | 12585858
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- Benzofurans
- Melanins
- linderol A
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Topics |
- Benzofurans
(analysis, chemical synthesis, pharmacology)
- Cells, Cultured
(drug effects)
- Crystallography, X-Ray
- Lindera
(chemistry)
- Melanins
(biosynthesis)
- Melanoma, Experimental
(metabolism)
- Molecular Structure
- Plants, Medicinal
(chemistry)
- Stereoisomerism
- Tumor Cells, Cultured
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