cis-Arenediols as versatile chiral synthons in the synthesis of prostaglandins, cyclitols, carbohydrates, and alkaloids

Simple item page
dc.contributor.authorContla, Hector Lunaen
dc.contributor.committeechairHudlicky, Tomasen
dc.contributor.committeememberMerola, Joseph S.en
dc.contributor.committeememberMason, John G.en
dc.contributor.committeememberWhite, Robert H.en
dc.contributor.committeememberBecker, David A.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:16:30Zen
dc.date.adate2008-07-28en
dc.date.available2014-03-14T21:16:30Zen
dc.date.issued1992-09-15en
dc.date.rdate2008-07-28en
dc.date.sdate2008-07-28en
dc.description.abstractThe oxidation of simple benzene derivatives by a mutant of Pseudomonas putida, called 39-D, produces cis-arenediols (1). The diols are enantiomerically pure and can be used as synthons for the preparation of a variety of interesting compounds because of their stereochemistry and the special array of functional groups. See: Figure 1 cis -Toluenedio] (2) served as a chiral intermediate in an efficient synthesis of enone (3). which has been used to attain prostaglandin Fra and Neplanocin A. The same diol (2) was transformed into both enantiomers of a terpene synthon (4). See: Figures 2, 3, 4 Oxidative functionalization of cis-chlorobenzenediol (5) afforded intermediates suitable for transformation into L-erythrose (6), conduritol C (7), dihydroconduritol C (8) and aminoconduntol F-4 (9). See: Figures 5, 6, 7, 8 The application of this versatile synthetic protocol culminated in an approach to kifunensine (10), an important glycosidase inhibitor, which was approached according to the following retrosynthetic analysis: See: Figures 10, 11, 12, 5, 14, 13 A detailed study of the nucleophilic opening of epoxide 13 was carried out in order to better understand the parameters of the diastereoselective functionalization of arenediols. Details are provided for the oxidative functionalization of chlorobenzenediol (5), the key compound in all of the projects discussed.en
dc.description.degreePh. D.en
dc.format.extentvi, 195 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-07282008-134713en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-07282008-134713/en
dc.identifier.urihttp://hdl.handle.net/10919/38900en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V856_1991.C667.pdfen
dc.relation.isformatofOCLC# 26248016en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V856 1991.C667en
dc.subject.lcshAlkaloids -- Synthesisen
dc.subject.lcshCarbohydrates -- Synthesisen
dc.subject.lcshChemistry, Organicen
dc.subject.lcshCyclic compounds -- Synthesisen
dc.subject.lcshOrganic compounds -- Synthesisen
dc.subject.lcshProstaglandins -- Synthesisen
dc.titlecis-Arenediols as versatile chiral synthons in the synthesis of prostaglandins, cyclitols, carbohydrates, and alkaloidsen
dc.typeDissertationen
dc.type.dcmitypeTexten
thesis.degree.disciplineChemistryen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.leveldoctoralen
thesis.degree.namePh. D.en

Files

Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
LD5655.V856_1991.C667.pdf
Size:
9.6 MB
Format:
Adobe Portable Document Format
Description:
Download

Collections

Doctoral Dissertations