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Total Synthesis of Carpacin and its Geometric Isomer as a Cancer Chemopreventer
Author(s) -
Tseng TsuiHwa,
Tsheng YenMin,
Lee YeanJang,
Hsu HsingLing
Publication year - 2000
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200000157
Subject(s) - chemistry , wittig reaction , aryl , yield (engineering) , reagent , sesamol , coupling reaction , palladium , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , alkyl , materials science , metallurgy , antioxidant
Abstract Carpacin ( 1a ), an antidepressant in Asiatic folk medicine from the Carpano tree, is achieved in which the longest linear sequence is only four steps in over all yield 67% from commercially available Sesamol. The key transformations in the synthesis are the selective palladium‐catalyzed coupling reactions of aryl bromide with Grignard reagents. The first preparation of its geometric isomer ( 1b ) is described. Highlights of the synthesis include Pd‐catalyzed coupling, selective hydrogenation, and Wittig reactions. Carpacin was examined as a potential inhibitor of carcinogenesis.