서지주요정보
Synthetic studies on lactacystin, trichodimerol and Lasonolide A = 락타시스틴과 트리코디메롤과 라소놀라이드 A의 합성에 대한 연구
서명 / 저자 Synthetic studies on lactacystin, trichodimerol and Lasonolide A = 락타시스틴과 트리코디메롤과 라소놀라이드 A의 합성에 대한 연구 / Hyuk-Sang Jun.
저자명 Jun, Hyuk-Sang ; 전혁상
발행사항 [대전 : 한국과학기술원, 2001].
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소장정보

등록번호

8012220

소장위치/청구기호

학술문화관(문화관) 보존서고

DCH 01012

SMS전송

도서상태

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반납예정일

초록정보

Synthesis of (+)-lactacystin 1 was accomplished in two different pathways. In the first approach, an enantioselective synthetic route to (+)-lactacystin 1 has been developed via several crucial steps, including amino hydroxylation of olefinic double bond in 116, the hydrolytic cyclization of 123, and regio- and stereo-selective functionalization of one hydroxymethyl group in 47. In the second approach, the synthetic route to (+)-lactacystin 1 has been established via several enantioselective steps, which culminated in diastereoselective crotylboration of 137c and hydroxy amination of allylic trichloroacetimidate 146 using mercurioamidation. For the synthesis of trichodimerol 159, a stereoselective synthetic route to an 8-membered ring 305, as a key intermediate, has been established. Fragmentation of bicyclo[3.3.1]nonane system has been developed to construct 8-membered carbocycle 305, which was achieved via asymmetric epoxidation followed by regioselective opening of 183 and dimerization of 311. For the synthesis of lasonolide A 318, a macrocyclic lactone 445 was synthesized efficiently via coupling of benzothiazol sulfone 447 and Z-α, β-unsaturated aldehyde 439. Benzothiazol sulfone 447 has been synthesized via iodocyclization of 347, Julia-type coupling of 404 and 405, and functionalization of hydroxyl group in 410. The synthesis of aldehyde 439 was achieved via an asymmetric crotylation followed by a diastereoselective allylation of 389, anionic cyclization of 393, and formation of Z-α, β-unsaturated ester 398.

서지기타정보

서지기타정보
청구기호 {DCH 01012
형태사항 iv, 110 p. : 삽도 ; 26 cm
언어 영어
일반주기 저자명의 한글표기 : 전혁상
지도교수의 영문표기 : Sung-Ho Kang
지도교수의 한글표기 : 강성호
수록잡지명 : "An enantiocontrolled synthesis of a key intermediate to (+)-lactacystin". Chem. Commun., , 1929-1930 (1998)
수록잡지명 : "An asymmetric synthetic route to (+)-lactacystin". Synlett., , 1045-1046 (1998)
학위논문 학위논문(박사) - 한국과학기술원 : 화학과,
서지주기 Reference : p. 107-110
주제 Lactacystin
Trichodimerol
Lasonolide
락타시스틴
트리코디메롤
라소놀라이드
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