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Progress Toward the Total Synthesis of Pilosanone C.
Progress Toward the Total Synthesis of Pilosanone C.
Contents Info
Progress Toward the Total Synthesis of Pilosanone C.
Material Type  
 학위논문
 
0017162206
Date and Time of Latest Transaction  
20250211151945
ISBN  
9798383593257
DDC  
540
Author  
Desmond, Jacob Anthony.
Title/Author  
Progress Toward the Total Synthesis of Pilosanone C.
Publish Info  
[S.l.] : Indiana University., 2024
Publish Info  
Ann Arbor : ProQuest Dissertations & Theses, 2024
Material Info  
268 p.
General Note  
Source: Dissertations Abstracts International, Volume: 86-02, Section: B.
General Note  
Advisor: Williams, David R.
학위논문주기  
Thesis (Ph.D.)--Indiana University, 2024.
Abstracts/Etc  
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.
Subject Added Entry-Topical Term  
Chemistry.
Subject Added Entry-Topical Term  
Analytical chemistry.
Subject Added Entry-Topical Term  
Organic chemistry.
Index Term-Uncontrolled  
Clerodane diterpenes
Index Term-Uncontrolled  
Pilosanones
Index Term-Uncontrolled  
Secondary metabolites
Index Term-Uncontrolled  
Quaternary carbon
Added Entry-Corporate Name  
Indiana University Chemistry
Host Item Entry  
Dissertations Abstracts International. 86-02B.
Electronic Location and Access  
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Control Number  
joongbu:656130
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