Enantioselective synthesis of 2,2,5-Tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans and synthesis of diketopiperazine containing natural products

dc.contributor.advisorMartin, Stephen Fen
dc.contributor.committeeMemberKrische, Michael Jen
dc.contributor.committeeMemberIverson, Brent Len
dc.contributor.committeeMemberBrodbelt, Jennifer Sen
dc.contributor.committeeMemberKerwin, Sean Men
dc.contributor.committeeMemberBielawski, Christopher Wen
dc.creatorBenjamin, Noah Meyeren
dc.date.accessioned2013-02-18T19:55:27Zen
dc.date.issued2012-12en
dc.date.submittedDecember 2012en
dc.date.updated2013-02-18T19:55:27Zen
dc.descriptiontexten
dc.description.abstractA chiral vinyl sulfoxide has been developed that undergoes highly diastereoselective Diels−Alder cycloadditions with various substituted furans in excellent yield. The cycloadducts can be stereoselectively transformed into tetrasubstituted tetrahydrofurans via ring-opening metathesis/cross-metathesis or oxidative cleavage and refunctionalization. A partial synthesis of the bioactive diketopiperazine containing natural product gliocladin C was achieved in nine steps, and 13.4% overall yield. The synthesis featured several novel transformations including the construction of the core structure by an elimination and nucleophilic addition sequence, followed by a Lewis acid promoted coupling with indole giving the key quaternary oxindole intermediate. A new protocol for intramolecular reductive coupling of the oxoindole and bis-unsaturated diketopiperazine led to successful construction of the hexacyclic skeleton.en
dc.description.departmentChemistryen
dc.format.mimetypeapplication/pdfen
dc.identifier.urihttp://hdl.handle.net/2152/19501en
dc.language.isoen_USen
dc.subjectDiketopiperazine, Tetrahydrofuran, Noah Benjaminen
dc.titleEnantioselective synthesis of 2,2,5-Tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans and synthesis of diketopiperazine containing natural productsen
thesis.degree.departmentChemistryen
thesis.degree.disciplineOrganic Chemistryen
thesis.degree.grantorThe University of Texas at Austinen
thesis.degree.levelDoctoralen
thesis.degree.nameDoctor of Philosophyen
Files
Original bundle
Now showing 1 - 1 of 1
Loading...
Thumbnail Image
Name:
Benjamin_Dissertation_20121.pdf
Size:
12.21 MB
Format:
Adobe Portable Document Format
License bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
2.13 KB
Format:
Plain Text
Description: