서지주요정보
Synthetic studies on (-)-allosamizoline = (-)-알로사미졸린 합성에 관한 연구
서명 / 저자 Synthetic studies on (-)-allosamizoline = (-)-알로사미졸린 합성에 관한 연구 / Eun-Ha Hoh.
발행사항 [대전 : 한국과학기술원, 1997].
Online Access 원문보기 원문인쇄

소장정보

등록번호

8007391

소장위치/청구기호

학술문화관(문화관) 보존서고

MCH 97030

휴대폰 전송

도서상태

이용가능

대출가능

반납예정일

리뷰정보

초록정보

Allosamidin exhibits inhibitory activity against chitinases. It has been thought that the chitinases inhibitor would be a good model for insect growth regulators. Allosamidin consists of 2 equivalents of N-acetyl-D-allosamine and 1 equivalent of a new aminocyclitol, named (-)-allosamizoline. For the synthesis of (-)-allosamizoline, two independent routes were attempted. In our first approach, synthesis of the key intermediate, hydroxymethyl-2-cyclopentene 41 was unsuccessful. In our second approach, cyclopentane 45 was chosen as a crucial intermediate, which could be formed via an intramolecular radical cyclization of phenyl selenoester. Prior to the main event to synthesize 45, we carried out a model study using D-glucose. Radical cyclization of phenyl selenoester 109 was employed as a key step. Treatment of 109 with tri-n-butyltinhydride in the presence of AIBN furnished a 10:1 mixture of cyclopentanes 110 and 111 in 60% yield. From the model study we ascertained that the radical cyclization of phenyl selenoester 124 would be applied successfully to the synthesis of (-)-allosamizoline.

서지기타정보

서지기타정보
청구기호 {MCH 97030
형태사항 ii, 36 p. : 삽도 ; 26 cm
언어 영어
일반주기 저자명의 한글표기 : 허은하
지도교수의 영문표기 : Sung-Ho Kang
지도교수의 한글표기 : 강성호
학위논문 학위논문(석사) - 한국과학기술원 : 화학과,
서지주기 Includes reference
주제 Radical cyclization of phenyl selenylester
(-)-Allosamizoline
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