Part 1. Modular Approach to Obtaining Diverse Tetrahydroquinoline-Derived Polycyclic Skeletons for Use in High-Throughput Generation of Natural-Product-like Chemical Probes

Download
  1. (PDF, 1 MB)
  2. Get@NRC: Part 1. Modular Approach to Obtaining Diverse Tetrahydroquinoline-Derived Polycyclic Skeletons for Use in High-Throughput Generation of Natural-Product-like Chemical Probes (Opens in a new window)
DOIResolve DOI: http://doi.org/10.1021/cc060055i
AuthorSearch for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for:
TypeArticle
Journal titleJ. Comb. Chem
ISSN15204766
Volume8
Issue5
Pages715734; # of pages: 20
AbstractA practical synthesis of a tetrahydroaminoquinoline scaffold (12) was developed that used a stereocontrolled aza Michael as the key reaction. Three tetrahydroquinoline alkaloid-like, tricyclic derivatives 16, 18, and 19 with different medium to macrocyclic ring skeletons were obtained, using this scaffold as the starting material, in a modular manner. The macrocyclic compounds with an isolated olefin and an electron-deficient olefin were obtained by ring-closing metathesis approaches. Compounds 16 and 18 are unique and contain bridged 10- and 12-membered functionalized rings. The NMR studies of these compounds revealed interesting information on the conformation of the bicyclic scaffolds that was dependent on the nature and the size of the macrocyclic rings. Finally, this modular methodology, using compound 21 anchored onto the solid support, successfully led to the generation of different macrocyclic derivatives, 23, 25, and 27 in solid-phase synthesis. The solid-phase synthesis approach outlined in this article has the potential to generate tetrahydroquinolinebased tricyclic compounds containing different medium to macrocyclic architectures.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier18517171
NPARC number12328027
Export citationExport as RIS
Report a correctionReport a correction
Record identifier2f5dc714-e290-4cfc-ad4a-2c335b9e71c1
Record created2009-09-10
Record modified2016-05-09
Bookmark and share
  • Share this page with Facebook (Opens in a new window)
  • Share this page with Twitter (Opens in a new window)
  • Share this page with Google+ (Opens in a new window)
  • Share this page with Delicious (Opens in a new window)