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Rapid Access to Csp3-Rich Bioisostere Scaffolds Through Photoredox Catalysis
Rapid Access to Csp3-Rich Bioisostere Scaffolds Through Photoredox Catalysis
Rapid Access to Csp3-Rich Bioisostere Scaffolds Through Photoredox Catalysis

Detailed Information

자료유형  
 학위논문 서양
최종처리일시  
20260202103205
ISBN  
9798280748804
DDC  
547
저자명  
Chen, Jingjia.
서명/저자  
Rapid Access to Csp3-Rich Bioisostere Scaffolds Through Photoredox Catalysis
발행사항  
[Sl] : Princeton University, 2025
발행사항  
Ann Arbor : ProQuest Dissertations & Theses, 2025
형태사항  
288 p
주기사항  
Source: Dissertations Abstracts International, Volume: 86-12, Section: B.
주기사항  
Advisor: MacMillan, David W. C.
학위논문주기  
Thesis (Ph.D.)--Princeton University, 2025.
초록/해제  
요약Drug development is a costly and time-intensive process, often taking a decade or more to advance a candidate molecule from discovery to market. Accelerating early-stage drug discovery-particularly the rapid synthesis of structurally diverse compounds for hit identification-is critical to reducing timelines and delivering life-saving therapeutics. Catalysis has emerged as a cornerstone of modern synthetic chemistry, enabling efficient, sustainable, and scalable methods for accessing complex molecules. Among these, photoredox catalysis has revolutionized organic synthesis over the past two decades by leveraging visible light to generate reactive intermediates from abundant precursors. This approach has unlocked unconventional bond disconnections and transformations that were previously inaccessible.This thesis explores photoredox catalytic strategies to incorporate aliphatic scaffolds-key structural motifs in pharmaceuticals-into drug-like molecules with enhanced efficiency. Chapter 2 details a streamlined method for synthesizing diverse 2-substituted bicyclo pentanes (BCPs), strained carbocycles of growing importance in medicinal chemistry as bioisosteres for para-substituted arenes. Chapter 3 introduces a mild, low-toxicity protocol for the synthesis of alkyl nitriles, versatile building blocks in drug development that are traditionally accessed via harsh, hazardous conditions. Together, these methodologies address long-standing synthetic challenges and provide practical tools for constructing high-value aliphatic architectures, offering potential applications in pharmaceutical discovery and beyond.
일반주제명  
Organic chemistry
일반주제명  
Chemistry
일반주제명  
Pharmaceutical sciences
일반주제명  
Analytical chemistry
키워드  
Bioisostere
키워드  
Catalysis
키워드  
Photoredox catalysis
키워드  
Radical chemistry
키워드  
Synthetic methodology
기타저자  
Princeton University Chemistry
기본자료저록  
Dissertations Abstracts International. 86-12B.
전자적 위치 및 접속  
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■24510▼aRapid  Access  to  Csp3-Rich  Bioisostere  Scaffolds  Through  Photoredox  Catalysis
■260    ▼a[Sl]▼bPrinceton  University▼c2025
■260  1▼aAnn  Arbor▼bProQuest  Dissertations  &  Theses▼c2025
■300    ▼a288  p
■500    ▼aSource:  Dissertations  Abstracts  International,  Volume:  86-12,  Section:  B.
■500    ▼aAdvisor:  MacMillan,  David  W.  C.
■5021  ▼aThesis  (Ph.D.)--Princeton  University,  2025.
■520    ▼aDrug  development  is  a  costly  and  time-intensive  process,  often  taking  a  decade  or  more  to  advance  a  candidate  molecule  from  discovery  to  market.  Accelerating  early-stage  drug  discovery-particularly  the  rapid  synthesis  of  structurally  diverse  compounds  for  hit  identification-is  critical  to  reducing  timelines  and  delivering  life-saving  therapeutics.  Catalysis  has  emerged  as  a  cornerstone  of  modern  synthetic  chemistry,  enabling  efficient,  sustainable,  and  scalable  methods  for  accessing  complex  molecules.  Among  these,  photoredox  catalysis  has  revolutionized  organic  synthesis  over  the  past  two  decades  by  leveraging  visible  light  to  generate  reactive  intermediates  from  abundant  precursors.  This  approach  has  unlocked  unconventional  bond  disconnections  and  transformations  that  were  previously  inaccessible.This  thesis  explores  photoredox  catalytic  strategies  to  incorporate  aliphatic  scaffolds-key  structural  motifs  in  pharmaceuticals-into  drug-like  molecules  with  enhanced  efficiency.  Chapter  2  details  a  streamlined  method  for  synthesizing  diverse  2-substituted  bicyclo  pentanes  (BCPs),  strained  carbocycles  of  growing  importance  in  medicinal  chemistry  as  bioisosteres  for  para-substituted  arenes.  Chapter  3  introduces  a  mild,  low-toxicity  protocol  for  the  synthesis  of  alkyl  nitriles,  versatile  building  blocks  in  drug  development  that  are  traditionally  accessed  via  harsh,  hazardous  conditions.  Together,  these  methodologies  address  long-standing  synthetic  challenges  and  provide  practical  tools  for  constructing  high-value  aliphatic  architectures,  offering  potential  applications  in  pharmaceutical  discovery  and  beyond.
■590    ▼aSchool  code:  0181.
■650  4▼aOrganic  chemistry
■650  4▼aChemistry
■650  4▼aPharmaceutical  sciences
■650  4▼aAnalytical  chemistry
■653    ▼aBioisostere
■653    ▼aCatalysis
■653    ▼aPhotoredox  catalysis
■653    ▼aRadical  chemistry
■653    ▼aSynthetic  methodology
■690    ▼a0490
■690    ▼a0485
■690    ▼a0486
■690    ▼a0572
■71020▼aPrinceton  University▼bChemistry.
■7730  ▼tDissertations  Abstracts  International▼g86-12B.
■790    ▼a0181
■791    ▼aPh.D.
■792    ▼a2025
■793    ▼aEnglish
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17357306▼nKERIS▼z이  자료의  원문은  한국교육학술정보원에서  제공합니다.

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