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Development and Application of New Synthetic Methods Inspired by the Total Synthesis of Natural Products
Development and Application of New Synthetic Methods Inspired by the Total Synthesis of Natural Products
상세정보
- 자료유형
- 학위논문 서양
- 최종처리일시
- 20260202103037
- ISBN
- 9798288863271
- DDC
- 547
- 서명/저자
- Development and Application of New Synthetic Methods Inspired by the Total Synthesis of Natural Products
- 발행사항
- [Sl] : University of California, Berkeley, 2025
- 발행사항
- Ann Arbor : ProQuest Dissertations & Theses, 2025
- 형태사항
- 707 p
- 주기사항
- Source: Dissertations Abstracts International, Volume: 87-01, Section: B.
- 주기사항
- Advisor: Sarpong, Richmond.
- 학위논문주기
- Thesis (Ph.D.)--University of California, Berkeley, 2025.
- 초록/해제
- 요약The following dissertation is presented in four chapters each examining individual research projects.Chapter 1 describes our initial efforts toward the total synthesis of the antiviral marine alkaloid dragmacidin F via an early stage deconstructive functionalization approach of 5-hydroxy-2- adamantanone to rapidly access the bicyclo[3.3.1]nonane core of the natural product. Further proposed steps include a Trofimov pyrrole synthesis followed by various C-H functionalization reactions to obtain the western fragment of the desired target molecule.Chapter 2 details the development and successful application of a novel oxidative C=N π-bond cleavage using photoexcited nitroarenes to convert ketoximes into their parent ketones. Given the importance of ketoximes as powerful directing groups, the practicality of this method is underscored in its use during a revised total synthesis of Cephalotaxus norditerpenoid cephanolide D. Additionally, a mechanistic study including isotopic labeling as well as an in-depth photophysical analysis is presented. Chapter 3 discusses a mechanistically driven development of a complementary reductive amination reaction, which reductively aminates the C-C σ-bond of carbonyls (as opposed to the carbonyl C-O π-bond) generating value-added linear and cyclic 3° amines in a modular fashion. Chapter 4 presents a novel and highly modular C-C cleavage /cross coupling strategy to access medium-to-large sized ring systems enabled by a strain release (ground state raising) and palladium-mediated templating approach. A variety of functional groups are tolerated in this reaction and the strategy could ultimately be employed in the total synthesis and structural revision of various resorcylic acid lactone (RAL) natural products. DFT calculations were used to support a proposed reaction mechanism.
- 일반주제명
- Organic chemistry
- 일반주제명
- Chemistry
- 기타저자
- University of California, Berkeley Chemistry
- 기본자료저록
- Dissertations Abstracts International. 87-01B.
- 전자적 위치 및 접속
- 로그인 후 원문을 볼 수 있습니다.
MARC
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■006m o d
■007cr#unu||||||||
■020 ▼a9798288863271
■035 ▼a(MiAaPQ)AAI31846628
■040 ▼aMiAaPQ▼cMiAaPQ
■0820 ▼a547
■1001 ▼aGottemann, Lucas Conrad Lothar Theodor.
■24510▼aDevelopment and Application of New Synthetic Methods Inspired by the Total Synthesis of Natural Products
■260 ▼a[Sl]▼bUniversity of California, Berkeley▼c2025
■260 1▼aAnn Arbor▼bProQuest Dissertations & Theses▼c2025
■300 ▼a707 p
■500 ▼aSource: Dissertations Abstracts International, Volume: 87-01, Section: B.
■500 ▼aAdvisor: Sarpong, Richmond.
■5021 ▼aThesis (Ph.D.)--University of California, Berkeley, 2025.
■520 ▼aThe following dissertation is presented in four chapters each examining individual research projects.Chapter 1 describes our initial efforts toward the total synthesis of the antiviral marine alkaloid dragmacidin F via an early stage deconstructive functionalization approach of 5-hydroxy-2- adamantanone to rapidly access the bicyclo[3.3.1]nonane core of the natural product. Further proposed steps include a Trofimov pyrrole synthesis followed by various C-H functionalization reactions to obtain the western fragment of the desired target molecule.Chapter 2 details the development and successful application of a novel oxidative C=N π-bond cleavage using photoexcited nitroarenes to convert ketoximes into their parent ketones. Given the importance of ketoximes as powerful directing groups, the practicality of this method is underscored in its use during a revised total synthesis of Cephalotaxus norditerpenoid cephanolide D. Additionally, a mechanistic study including isotopic labeling as well as an in-depth photophysical analysis is presented. Chapter 3 discusses a mechanistically driven development of a complementary reductive amination reaction, which reductively aminates the C-C σ-bond of carbonyls (as opposed to the carbonyl C-O π-bond) generating value-added linear and cyclic 3° amines in a modular fashion. Chapter 4 presents a novel and highly modular C-C cleavage /cross coupling strategy to access medium-to-large sized ring systems enabled by a strain release (ground state raising) and palladium-mediated templating approach. A variety of functional groups are tolerated in this reaction and the strategy could ultimately be employed in the total synthesis and structural revision of various resorcylic acid lactone (RAL) natural products. DFT calculations were used to support a proposed reaction mechanism.
■590 ▼aSchool code: 0028.
■650 4▼aOrganic chemistry
■650 4▼aChemistry
■653 ▼aMethod development
■653 ▼aTotal synthesis of natural products
■653 ▼aAmination reaction
■690 ▼a0490
■690 ▼a0485
■71020▼aUniversity of California, Berkeley▼bChemistry.
■7730 ▼tDissertations Abstracts International▼g87-01B.
■790 ▼a0028
■791 ▼aPh.D.
■792 ▼a2025
■793 ▼aEnglish
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17356799▼nKERIS▼z이 자료의 원문은 한국교육학술정보원에서 제공합니다.
