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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 39, Number 2
JKCSEZ 39(2)
April 20, 1995 

 
Title
Synthesis of 14-Membered Phenylthio Enediyne Lactone: A Precursor of the Potential Enediyne Antitumor Antibiotics

항암작용 가능성이 있는 10-Membered Enediyne의 선구물질인 14-Membered Phenylthio Enediyne Lactone 의 합성
Author
Kee Dong Kim

김기동
Keywords
Abstract
본 연구에서는 항암제로서의 가능성이 있는 10-membered enediyne(6)의 선구물질로 사용될 수 있는 14-membered phenylthio enediyne lactone을 성공적으로 합성할 수 있었다. 14-membered lactone은 Ireland-Claisen rearrangement에 의해 10-membered enediyne(11)으로 변환되며 이 물질(11)은 최종물질(8)로 전환될 수 있을 것으로 예상된다. 이 14-membered enediyned Lactone(23)은 DCC/PTSA/Pyridine 하에 enediyne hydroxy acid(22)의 락톤화 반응에 의해 합성되었다. Enediyne hydroxy acid는 Pd(0) 촉매하에 methyl pentynoate(19)와 enyne alcohol(17)을 cis-1,2-dichloroethylene과 연속적으로 coupling 반응을 하여 좋은 수득율로 얻을 수 있었다. 그 때 필요한 enyne alcohol(17)은 vinyltin(12)을 출발물질로 하여 성공적으로 얻을 수 있었다.

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.

Page
103 - 110
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