Synthesis of a key intermediate to 1β-methylcarbapenem antibiotics via iodoamidation = 요오드아미드화반응을 이용한 항생제 1베타-메틸카바페넴의 중요중간체의 합성

Cited 0 time in webofscience Cited 0 time in scopus
  • Hit : 217
  • Download : 0
A stereoselective synthesis of the key intermediate 8 of 1β-methylcarbapenem antibiotics was accomplished. The key features of the scheme include the stereoselective iodoamidation of Z-olefinic allylic alcohol 76 and the regioselective ring opening of aziridine 80c with cyanide. Z-olefinic allylic alcohol 76 was prepared by Wittig reaction of phosphonium salt 74 and aldehyde 71, then transformed into the desired cis-aziridine 80c by stereoselective iodoamidation, acidic hydrolysis and cyclization in sequence. Aziridine 80c was ring-opened with moderate regioselectivity by cyanide in 70% yield employing the freshly generated LiCN-HMPA reagent. Formation of b-lactam 96 from amide 95 was unexpectedly accomplished by its treatment with di-t-butyl dicarbonate. The prepared b-lactam 96 was detosylated at low temperature, then the primary hydroxy group was unmasked. Azitidinone alcohol 33 was converted into the desired product 8 by oxidation with PDC.
Advisors
Kang, Sung-Horesearcher강성호researcher
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1999
Identifier
151664/325007 / 000973088
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1999.2, [ ii, 46 p. ]

Keywords

beta-lactam; Aziridine; Iodoamidation; β-methylcarbapenem; Imidate; 이미데이트; 베타락탐; 아지리딘; 요오드아미드화반응; 1베타-메틸카바페넴

URI
http://hdl.handle.net/10203/31805
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=151664&flag=dissertation
Appears in Collection
CH-Theses_Master(석사논문)
Files in This Item
There are no files associated with this item.

qr_code

  • mendeley

    citeulike


rss_1.0 rss_2.0 atom_1.0