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KMID : 1059519950390020103
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Journal of the Korean Chemical Society
1995 Volume.39 No. 2 p.103 ~ p.110
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Synthesis of 14-Membered Phenylthio Enediyne Lactone : A Precursor of the Potential Enediyne Antitumor Antibiotics
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Kim Kee-Dong
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Abstract
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Phenylthio substituted 14-membered lactone(23) which can serve as a precursor of a potential antitumor antibiotics (6), was successfully prepared. The synthesis of the lactone was accomplished via lactonization of the corresponding enediyne hydroxy acid (22). This hydroxy acid was derived from Pd(0)-catalyzed coupling reaction of methyl pentynoate and cis-1,2-dichloroethylene followed by another Pd(0)-catalyzed coupling reaction of the resulting methyl chloroenyne ester (20) and enyneol (17). The required enyne alcohol was successfully synthesized from vinyltin compound (12) in good overall yield.
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