Synthetic studies on (-)-allosamizoline = (-)-알로사미졸린 합성에 관한 연구

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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.
Advisors
Kang, Sung-Horesearcher강성호researcher
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1997
Identifier
112886/325007 / 000953655
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1997.2, [ ii, 36 p. ]

Keywords

Radical cyclization of phenyl selenylester; (-)-Allosamizoline

URI
http://hdl.handle.net/10203/32779
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=112886&flag=dissertation
Appears in Collection
CH-Theses_Master(석사논문)
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