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Progress Toward the Total Synthesis of Pilosanone C
Progress Toward the Total Synthesis of Pilosanone C
Progress Toward the Total Synthesis of Pilosanone C

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자료유형  
 학위논문 서양
최종처리일시  
20250211151945
ISBN  
9798383593257
DDC  
540
저자명  
Desmond, Jacob Anthony.
서명/저자  
Progress Toward the Total Synthesis of Pilosanone C
발행사항  
[Sl] : Indiana University, 2024
발행사항  
Ann Arbor : ProQuest Dissertations & Theses, 2024
형태사항  
268 p
주기사항  
Source: Dissertations Abstracts International, Volume: 86-02, Section: B.
주기사항  
Advisor: Williams, David R.
학위논문주기  
Thesis (Ph.D.)--Indiana University, 2024.
초록/해제  
요약Clerodane diterpenes are a large family of secondary metabolites found in hundreds of plant species and prokaryotes. Since 1990, many examples of the clerodane family have been isolated and characterized. Representative compounds are known to possess significant biological properties, notably, insect antifeedant, opioid receptor agonist and hallucinogenic. The basic structure of clerodanes are bicyclic diterpenoids which primarily exist as a 6-6 ring system. The pilosanones are a subset of the clerodane family which contain a unique 6-7 bicylo[5.4.0]undecane ring system. Pilosanone C 1 has a characteristic oxabicyclo[3.2.1]octene core with four contiguous stereocenters, one of which is a quaternary carbon. There are no reports of synthesis studies in pursuit of this target. Much progress has been made in our laboratories to synthesize the natural product including a route to attempt a late-stage metal catalyzed stereoselective [4+3] cyclization, an early stage intramolecular oxidopyrylium [5+2] cycloaddition, and a chiral pool strategy beginning with (R)-(−)-Carvone.
일반주제명  
Chemistry
일반주제명  
Analytical chemistry
일반주제명  
Organic chemistry
키워드  
Clerodane diterpenes
키워드  
Pilosanones
키워드  
Secondary metabolites
키워드  
Quaternary carbon
기타저자  
Indiana University Chemistry
기본자료저록  
Dissertations Abstracts International. 86-02B.
전자적 위치 및 접속  
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■020    ▼a9798383593257
■035    ▼a(MiAaPQ)AAI31327645
■040    ▼aMiAaPQ▼cMiAaPQ
■0820  ▼a540
■1001  ▼aDesmond,  Jacob  Anthony.▼0(orcid)0009-0007-9070-371X
■24510▼aProgress  Toward  the  Total  Synthesis  of  Pilosanone  C
■260    ▼a[Sl]▼bIndiana  University▼c2024
■260  1▼aAnn  Arbor▼bProQuest  Dissertations  &  Theses▼c2024
■300    ▼a268  p
■500    ▼aSource:  Dissertations  Abstracts  International,  Volume:  86-02,  Section:  B.
■500    ▼aAdvisor:  Williams,  David  R.
■5021  ▼aThesis  (Ph.D.)--Indiana  University,  2024.
■520    ▼aClerodane  diterpenes  are  a  large  family  of  secondary  metabolites  found  in  hundreds  of  plant  species  and  prokaryotes.  Since  1990,  many  examples  of  the  clerodane  family  have  been  isolated  and  characterized.  Representative  compounds  are  known  to  possess  significant  biological  properties,  notably,  insect  antifeedant,  opioid  receptor  agonist  and  hallucinogenic.  The  basic  structure  of  clerodanes  are  bicyclic  diterpenoids  which  primarily  exist  as  a  6-6  ring  system.  The  pilosanones  are  a  subset  of  the  clerodane  family  which  contain  a  unique  6-7  bicylo[5.4.0]undecane  ring  system.  Pilosanone  C  1  has  a  characteristic  oxabicyclo[3.2.1]octene  core  with  four  contiguous  stereocenters,  one  of  which  is  a  quaternary  carbon.  There  are  no  reports  of  synthesis  studies  in  pursuit  of  this  target.  Much  progress  has  been  made  in  our  laboratories  to  synthesize  the  natural  product  including  a  route  to  attempt  a  late-stage  metal  catalyzed  stereoselective  [4+3]  cyclization,  an  early  stage  intramolecular  oxidopyrylium  [5+2]  cycloaddition,  and  a  chiral  pool  strategy  beginning  with  (R)-(−)-Carvone.
■590    ▼aSchool  code:  0093.
■650  4▼aChemistry
■650  4▼aAnalytical  chemistry
■650  4▼aOrganic  chemistry
■653    ▼aClerodane  diterpenes
■653    ▼aPilosanones
■653    ▼aSecondary  metabolites
■653    ▼aQuaternary  carbon
■690    ▼a0485
■690    ▼a0486
■690    ▼a0490
■71020▼aIndiana  University▼bChemistry.
■7730  ▼tDissertations  Abstracts  International▼g86-02B.
■790    ▼a0093
■791    ▼aPh.D.
■792    ▼a2024
■793    ▼aEnglish
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17162206▼nKERIS▼z이  자료의  원문은  한국교육학술정보원에서  제공합니다.

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