Solution- and Solid-Phase Synthesis of Natural Product-Like Tetrahydroquinoline-Based Polycyclics Having a Medium Size Ring

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DOIResolve DOI: http://doi.org/10.1021/cc049935s
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TypeArticle
Journal titleJournal of Combinatorial Chemistry
ISSN1520-4766
Volume6
Issue5
Pages735745; # of pages: 11
AbstractA solid-phase synthesis of tetrahydroquinoline-derived polycyclic 4, having a medium size ring with an enamide functionality, was achieved from tetrahydroquinoline derivative 3 in five steps with overall 40- 45% yield. An enantiopure, tetrahydroquinoline-derived �-amino ester, 1, was converted into compound 2 that has a free phenolic hydroxyl group as an anchoring site for solid-phase synthesis. The solid-phase worked well for this sequence, in which the synthesis of the unsaturated eight-membered enamide lactam was obtained by a ring-closing metathesis approach. Compound 4 is a novel, natural product-like polycyclic derivative that could further be utilized in library generation for developing small molecule chemical probes.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier18517171
NPARC number12340900
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Record identifierb971cfa3-41a3-48cd-b8d6-bebd0ede35b5
Record created2009-09-11
Record modified2016-05-09
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