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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.

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.
AuthorsMasayuki Yamashita, Nobukazu Ohta, Takashi Shimizu, Kayoko Matsumoto, Yoko Matsuura, Ikuo Kawasaki, Tetsuaki Tanaka, Naoyoshi Maezaki, Shunsaku Ohta
JournalThe Journal of organic chemistry (J Org Chem) Vol. 68 Issue 4 Pg. 1216-24 (Feb 21 2003) ISSN: 0022-3263 [Print] United States
PMID12585858 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Benzofurans
  • Melanins
  • linderol A
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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