METHOD FOR TOTAL SYNTHESIZING &alpha；-PYRONE DERIVATIVES USING BY GOLD CATALYST AND &alpha；-PYRONE DERIVATIVES HAVING CYTOTOXICITY AGAINST HUMAN CANCER CELL SYNTHESIZED THEREBY
KOREA INSTITUTE OF OCEAN SCIENCE & TECHNOLOGY;한국해양과학기술원
发明人:
LEE, JONG SEOK,이종석,SHIN, JUN HO,신준호,LEE, HYI SEUNG,이희승,SHIN, HEE JAE,신희재,LEE, YEON JU,이연주,LEE, JONG SEOKKR,SHIN, JUN HOKR,LEE, HYI SEUNGKR,SHIN, HEE JAEKR,LEE, YEON JUKR
申请号：
KR1020140194039
公开号：
KR1020160080799A
申请日:
2014.12.30
申请国别(地区):
KR
年份:
2016
代理人:
摘要：
The present invention relates to a method for total synthesis of an &alpha；-pyrone derivative comprises preparing a &beta；-ketoester compound starting from butanol through the Witting olefin reaction, Swern oxidation reaction, Corey-Fuchs reaction and Claisen condensation, and subjecting the &beta；-ketoester compound to 6-endo-dig intramolecular cyclization using a gold catalyst to form an &alpha；-pyrone ring and to carry out total synthesis of an &alpha；-pyrone derivative. The &alpha；-pyrone derivative obtained by the total synthesis method is (+)-violapyrone C having the same shape as the naturally occurring &alpha；-pyrone derivative and has cytotoxicity against at least 10 human cancer cell lines, and thus can be useful as an anti-cancer agent.본 발명에 따른 금 촉매를 이용한 α-피론 유도체 전합성 방법은, 부탄올을 출발물질로 하여 크게, 위팅 올레핀 반응(Witting olefin reaction), 스웬 산화반응(Swern oxidation reaction), 코리-푹스 반응(Corey-Fuchs reaction), 클라이센 축합반응(Claisen condensation)을 거쳐 제조된 β-케토 에스테르 화합물에 금(gold) 촉매를 이용한 6-endo-dig 분자내 고리화 반응을 통해 α-피론 고리 (α-pyrone ring)를 형성시켜 α-피론 유도체를 전합성(total synthesis)할 수 있다.상기한 전합성 방법에 의해 제조된 α-피론 유도체는 자연 상에서 존재하는 α-피론 유도체와 동일한 형태를 가지는 (+)-바이올라피론 C((+)-violapyrone C)이며, 10 종 이상의 인간암세포주(human cancer cell line)에 세포독성(cytotoxicity)을 가져 암치료제로 유용하게 이용될 수 있다.
