Synthetic & computational studies towards conidiogenone B : unexpected selectivity of intramolecular [3+2] TMM diyl-olefin cycloaddition = 코니디오지논 B에 대한 합성적 & 계산화학적 연구 : 분자내 [3+2] TMM 다이라디칼-올레핀 고리화반응의 새로운 선택성unexpected selectivity of intramolecular [3+2] TMM diyl-olefin cycloaddition

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Total synthesis of tetracyclic diterpene natural product, conidiogenone B, has been attempted, which is known for its anticancer and antibacterial activity. Key-steps include Eschenmoser-Tanabe fragmentation, Wang allenation, and intramolecular [3+2] TMM diyl-olefin cycloaddition reaction. To our surprise, a bridged isomer, rather than a linear isomer, has been obtained from the cycloaddition, which led us to revise the synthetic approach and to conduct model studies. The synthetic and computational model studies revealed that an extra methyl group on TMM diyl and/or an electron-withdrawing group on olefin, can dictate the regioselectivity of the cycloaddition.
Advisors
Lee, Hee-Yoonresearcher이희윤researcher
Description
한국과학기술원 :화학과,
Publisher
한국과학기술원
Issue Date
2020
Identifier
325007
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2020.2,[i, 85 p. :]

Keywords

Total Synthesis▼aNatural Product▼aTrimethylenemethane (TMM)▼aDiradical▼aTandem Reaction▼aPolycyclic Structure▼aCycloaddition▼aDensity Functional Theory; 전합성▼a천연물▼aTrimethylenemethane (TMM)▼a다이라디칼▼a쌍라디칼▼a텐덤 반응▼a다환 구조▼a고리화 첨가반응▼a밀도범함수

URI
http://hdl.handle.net/10203/283534
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=907045&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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