서지주요정보
Synthetic studies toward total synthesis of Nopsan-4-ol and Delnudine = 놉산-4-올과 델누딘의 전합성에 관한 연구
서명 / 저자 Synthetic studies toward total synthesis of Nopsan-4-ol and Delnudine = 놉산-4-올과 델누딘의 전합성에 관한 연구 / Se-Jin Lee.
저자명 Lee, Se-Jin ; 이세진
발행사항 [대전 : 한국과학기술원, 2004].
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8015411

소장위치/청구기호

학술문화관(문화관) 보존서고

DCH 04001

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초록정보

Development of new synthetic methodologies and their applications to the total synthesis of natural products were studied. In the course of synthesis of tricyclo-[4.3.2.$0^{1,5}$] undecane structure, unusual 6-exo radical cyclization was observed. Most of 2,2-disubstituted cyclopentene derivatives cyclized to produce tricyclo-[4.3.2.$0^{1,5}$] undecane through radical reaction sequence, which involved cyclopropyl methyl radical mediated rearrangement. However, in the case of 146a, unusual 6-exo-radical cyclization proceeded due to stereochemistry of secondary hydroxyl group. Tricyclic 151, prepared from β-keto ester 136, was used as a key intermediate for the total synthesis of Nopsan-4-ol. 151 was converted to Nopsan-4-ol by introduction of methyl group via 1,4-addition at C-6, methylation at C-4 position, and stereoselective reduction of olefin. Synthetic method used in the construction of tricyclo-[4.3.2.$0^{1,5}$] undecane was also applied to the total synthesis of Delnudine. BC-ring of Delnudine was prepared through that radical cyclization and rearrangement. After manipulation of functional groups of B-ring, A-ring of Delnudine was prepared through a regioselective alkylidene carbene C-H insertion derived from alkylation of trimethylsilyl-diazomethyl lithium followed by Peterson olefination and α -elimination, and then ozonolysis followed by aldol condensation of resulting cyclopentene. Some manipulations of A-ring were studied to introduce a functional group on unactivated C-18 position. A noteworthy aspect of this synthesis is a one-pot construction of tricyclic ring system.

서지기타정보

서지기타정보
청구기호 {DCH 04001
형태사항 iii, 145 p. : 삽도 ; 26 cm
언어 영어
일반주기 저자명의 한글표기 : 이세진
지도교수의 영문표기 : Hee-Yoon Lee
지도교수의 한글표기 : 이희윤
학위논문 학위논문(박사) - 한국과학기술원 : 화학과,
서지주기 Reference : p. 138-145
주제 NOPSAN-4-OL
DELNUDINE
TOTAL SYNTHESIS
RADICAL
CYCLIZATION REACTION
놉산-4-올
델누딘
전합성
라디칼
고리화반응
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