서지주요정보
Stereoselective amination of 4-penten-1,2,3-triols; its synthetic application to (-)-anisomycin and (+)-polyoxamic acid = 4-펜텐-1,2,3-트리올의 입체선택적인 아민화 반응과 이를 이용한 (-)-아니 소마이신과 (+)-폴리옥사믹산의 합성
서명 / 저자 Stereoselective amination of 4-penten-1,2,3-triols; its synthetic application to (-)-anisomycin and (+)-polyoxamic acid = 4-펜텐-1,2,3-트리올의 입체선택적인 아민화 반응과 이를 이용한 (-)-아니 소마이신과 (+)-폴리옥사믹산의 합성 / Hyeong-Wook ChoiI.
저자명 Choi, Hyeong-Wook ; 최형욱
발행사항 [대전 : 한국과학기술원, 1996].
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소장정보

등록번호

8006771

소장위치/청구기호

학술문화관(문화관) 보존서고

MCH 96026

SMS전송

도서상태

이용가능

대출가능

반납예정일

초록정보

The double bond of (2S, 3S)-4-penten-1,2,3-triol 28, which was readily prepared from dimethyl L-tartrate in 67% overall yield, was iodoaminated stereoselectively by treating its tris(trichloroacetimidate) with iodine monobromide. Also that of (2R, 3S)-4-penten-1,2,3-triol 84, which was produced from lactone 87 in 68% overall yield, was functionalized into amino iodide stereoselectively by cyclizing its tris(trichloroacetimidate) with iodine. After acidic hydrolysis of the cyclized products followed by protection as t-butyl carbamate, the former and the latter stereoselectivity were determined to be 37: 1 and 38: 1 in favor of (2S, 3S, 4S)- and (2R, 3S, 4S)-4-amino-5-iodo-1,2,3-triol, respectively. Since (-)-anisomycin 30 and (+)-polyoxamic acid 31 contain the fucntional groups of carbamate 29, their syntheses were accomplished efficiently from 29. Carbamate 29 was converted into triol 112 via its protection as acetonide, aziridine formation and cuprate reaction. Cyclization of 112 into pyrrolidine 104 proceeded smoothly under Mitsunobu conditions in the presence of PPTS. The adjustment of its functional groups established the synthesis of (-)-anisomycin 30. Monosilylation followed by acetonide formation gave iodide 116. Treatment of 116 with acetate generated oxazolidinone, of which protection and hydrolysis provided alcohol 119. The synthesis of (+)-polyoxamic acid 31 was completed by oxidation of 119 followed by acidic hydrolysis.

서지기타정보

서지기타정보
청구기호 {MCH 96026
형태사항 iii, 53 p. : 삽도 ; 22 cm
언어 영어
일반주기 저자명의 한글표기 : 최형욱
지도교수의 영문표기 : Sung-Ho Kang
지도교수의 한글표기 : 강성호
학위논문 학위논문(석사) - 한국과학기술원 : 화학과,
서지주기 Reference : p. 51-53
주제 Iodoamination
4-Penten-1,2,3-triol
(-)-Anisomycin
(+)-Polyoxamic acid
요드아민화반응
4-펜텐-1,2,3-트리올
(-)-아니소마이신
(+)-폴리옥사믹산
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