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A Divergent Approach to Mono-THF Acetogenins: Total Synthesis of cis-Solamin A and B via the Traceless Petasis Reaction
A Divergent Approach to Mono-THF Acetogenins: Total Synthesis of cis-Solamin A and B via the Traceless Petasis Reaction
상세정보
- 자료유형
- 학위논문 서양
- 최종처리일시
- 20260202104805
- ISBN
- 9798291584477
- DDC
- 547
- 서명/저자
- A Divergent Approach to Mono-THF Acetogenins: Total Synthesis of cis-Solamin A and B via the Traceless Petasis Reaction
- 발행사항
- [Sl] : Northwestern University, 2025
- 발행사항
- Ann Arbor : ProQuest Dissertations & Theses, 2025
- 형태사항
- 181 p
- 주기사항
- Source: Dissertations Abstracts International, Volume: 87-03, Section: B.
- 주기사항
- Advisor: Thomson, Regan J.
- 학위논문주기
- Thesis (Ph.D.)--Northwestern University, 2025.
- 초록/해제
- 요약Annonaceous acetogenins are a biologically significant class of polyketide natural products known for their potent inhibition of mitochondrial Complex I and potential anticancer properties. This dissertation presents the total synthesis of cis-solamin A and B, two representative members of the mono-THF acetogenin subclass, and the development of a versatile platform for analogue generation. A key step in the synthesis utilized the Thomson Research Group's traceless Petasis reaction for the stereoselective construction of allenols, which underwent gold-catalyzed cyclization to form the tetrahydrofuran core. Strategic Grignard additions, late-stage ruthenium-catalyzed butenolide annulation, and efficient access to D-glyceraldehyde from D-mannitol enabled the completion of both targets. The resulting approach offers a scalable and modular route to mono-THF acetogenins and lays the foundation for future structure-activity relationship studies.
- 일반주제명
- Organic chemistry
- 일반주제명
- Chemistry
- 일반주제명
- Physical chemistry
- 키워드
- Total synthesis
- 기타저자
- Northwestern University Chemistry
- 기본자료저록
- Dissertations Abstracts International. 87-03B.
- 전자적 위치 및 접속
- 로그인 후 원문을 볼 수 있습니다.
MARC
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■1001 ▼aNguyen, Huong Quynh Anh.▼0(orcid)0000-0002-9907-8275
■24512▼aA Divergent Approach to Mono-THF Acetogenins: Total Synthesis of cis-Solamin A and B via the Traceless Petasis Reaction
■260 ▼a[Sl]▼bNorthwestern University▼c2025
■260 1▼aAnn Arbor▼bProQuest Dissertations & Theses▼c2025
■300 ▼a181 p
■500 ▼aSource: Dissertations Abstracts International, Volume: 87-03, Section: B.
■500 ▼aAdvisor: Thomson, Regan J.
■5021 ▼aThesis (Ph.D.)--Northwestern University, 2025.
■520 ▼aAnnonaceous acetogenins are a biologically significant class of polyketide natural products known for their potent inhibition of mitochondrial Complex I and potential anticancer properties. This dissertation presents the total synthesis of cis-solamin A and B, two representative members of the mono-THF acetogenin subclass, and the development of a versatile platform for analogue generation. A key step in the synthesis utilized the Thomson Research Group's traceless Petasis reaction for the stereoselective construction of allenols, which underwent gold-catalyzed cyclization to form the tetrahydrofuran core. Strategic Grignard additions, late-stage ruthenium-catalyzed butenolide annulation, and efficient access to D-glyceraldehyde from D-mannitol enabled the completion of both targets. The resulting approach offers a scalable and modular route to mono-THF acetogenins and lays the foundation for future structure-activity relationship studies.
■590 ▼aSchool code: 0163.
■650 4▼aOrganic chemistry
■650 4▼aChemistry
■650 4▼aPhysical chemistry
■653 ▼aMethodology development
■653 ▼aNatural product synthesis
■653 ▼aOrganic synthesis
■653 ▼aSmall-molecule synthesis
■653 ▼aStructure elucidation
■653 ▼aTotal synthesis
■690 ▼a0490
■690 ▼a0485
■690 ▼a0494
■71020▼aNorthwestern University▼bChemistry.
■7730 ▼tDissertations Abstracts International▼g87-03B.
■790 ▼a0163
■791 ▼aPh.D.
■792 ▼a2025
■793 ▼aEnglish
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17358881▼nKERIS▼z이 자료의 원문은 한국교육학술정보원에서 제공합니다.
