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Virginia Tech

The enantioselective synthesis of C₁₈-sphingosines

Abstract

dc:description.abstract

Biocatalytic conversion of chlorobenzene to the corresponding homochiral cyclohexadiene cis-diol (113) allows, through careful symmetry-based planning, the stereodivergent synthesis of all sphingosine stereoisomers. This was achieved via the selective preparation of the appropriate diastereomer of azido alcohol (118), were C-4 and C-5 correspond to C-3 and C-2 of the sphingosine skeleton, respectively (Scheme 1).

Degree

thesis:*
Name thesis:degree_name
Ph. D.
Level thesis:degree_level
doctoral
Discipline thesis:degree_discipline
Chemistry
Department dc:contributor.department
Chemistry
Grantor dc:publisher
Virginia Tech
Year dc:date.issued
1995

Author and committee

dc:creator, dc:contributor.*
Author dc:creator
  • Nugent, Thomas C.
Chair dc:contributor.committeechair
  • Hudlicky, Tomas
Committee members dc:contributor.committeemember
  • Tanko, James M.
  • White, Robert H.
  • Gibson, Harry W.
  • Brewer, Karen J.

Rights

dc:rights
Statement dc:rights
  • In Copyright
Language dc:language.iso
en

Identifiers

dc:identifier.*
Dc Identifier Other
etd-06062008-152643
OAI identifier oai:identifier
oai:vtechworks.lib.vt.edu:10919/38065

Chain of custody

source
Harvested from
Virginia Tech
Base URL
vtechworks.lib.vt.edu/oai/request
Last updated
2026-07-22
Source record
OAI-PMH GetRecord
related terms
citation

Nugent, Thomas C.. The enantioselective synthesis of C₁₈-sphingosines. doctoral thesis, Virginia Tech, 1995. http://hdl.handle.net/10919/38065