삭시톡신 합성을 위한 연구: 1,3-dihydro-2H-imidazol-2-one의 알데히드에 첨가반음

Title
삭시톡신 합성을 위한 연구: 1,3-dihydro-2H-imidazol-2-one의 알데히드에 첨가반음
Alternative Title
Studies directed toward the total synthesis of saxitoxin: Addition of 1,3-dihydro-2H-imidazol-2-one to aldehydes
Author(s)
이지훈; 류민석; 이희승; 이연주; 이종석
KIOST Author(s)
Lee, Jihoon(이지훈)Lee, Hyi Seung(이희승)Lee, Yeon Ju(이연주)Lee, Jong Seok(이종석)
Publication Year
2019-08-27
Abstract
Saxitoxin (STX, 1) is a highly toxic natural product, which is produced by several types of harmful dinoflagellates and accumulated in bivalves to intoxicate human being eventually. Due to the unique toxicity and the scarcity of analyticalSTX standard, development of a convenient synthetic pathway to this molecule has been an attractive project in the synthetic community.
In this report, we disclose our efforts to synthesize the carbon framework of STX with a proper functionalization utilizing an addition reaction of imidazol-2-one 2 with an aldehyde. The imidazolone 2 was prepared from 1-bromo-5-chloropentan-2-one in 5 steps. Mannich-type addition of 2 with benzylamine and ethyl glyoxalate 3 was investigated under various acidic conditions to find optimal reaction conditions. In most cases, the reactivities of 2 as a nucleophile were insufficient to produce the desired product in satisfactory levels of yields. However, the reaction conditionsutilizing PTSA as a catalyst proceeded with a useful level of yield.
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/22417
Bibliographic Citation
American Chemical Society 2019 Fall National Meeting, pp.1, 2019
Publisher
American Chemical Society
Type
Conference
Language
English
Publisher
American Chemical Society
Related Researcher
Research Interests

Marine Natural Products,Organic Chemistry,해양천연물,유기화학

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