Synthetic studies on swainsonine analogs = 스웬소닌 유도체의 합성에 관한 연구

We have investigated a new synthetic route to (-)-swainsonine and its analogs, which exhibited remarkable physiological effects including an immunoregulative activity. Iodoamination of γ-aminoalkene and allylic imidate was employed for the approach to their synthesis. However, the preparation of γ-aminoalkenes 45 and 56 was not so facile that iodocyclization of allylic imidate was prepared for the planned iodocyclization. Allylic alcohols 100A, 101A and 102A were readily derived from 79 which was obtained from Wittig olefination of lactol 78 and phosphonium salt 51B. Cyclization of allylic imidate of 100A, 101A and 102A was carried out in acetonitrile at 0℃-30℃ by using IBr as electrophile to furnish dihydrooxazole 100B, 101B and 102B, respectively. We made much efforts to convert the dihydrooxazole to (-)-swainsonine and its analogs, but successful results were not obtained.
Advisors
Kang, Sung-Horesearcher강성호researcher
Publisher
한국과학기술원
Issue Date
1994
Identifier
69170/325007 / 000923046
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1994.2, [ ii, 52 p. ]

URI
http://hdl.handle.net/10203/32657
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=69170&flag=t
Appears in Collection
CH-Theses_Master(석사논문)
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