Solution- and Solid-Phase, Modular Approaches for Obtaining Different Natural Product-Like Polycyclic Architectures from an Aminoindoline Scaffold for Combinatorial Chemistry

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DOIResolve DOI: http://doi.org/10.1021/cc0600573
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TypeArticle
Journal titleJournal of Combinatorial Chemistry
ISSN1520-4766
Volume8
Issue6
Pages856871; # of pages: 16
AbstractWith the goal of developing a modular approach leading to different indoline alkaloid natural-product-like tricyclic derivatives having an unsaturated lactam (see compounds 13, 14, and 16), an aminoindoline-based bicyclic scaffold 10 was obtained from 9. The selective deprotection of the indoline NTeoc or benzylic NHAlloc in compound 10, followed by N-acryloylation and then subjection to a ring-closing metathesis reaction, successfully led to obtaining two different architectures (13/14 and 16) having an unsaturated lactam functionality. This modular solution-phase methodology was then developed on solid phase. To achieve this objective, the aminoindoline bicyclic scaffold having an additional hydroxyl group could be immobilized onto the solid support using alkylsilyl linker-based polystyrene macrobeads, giving 18. By applying a ring-closing metathesis approach, 20 (tricyclic derivative with seven-membered-ring unsaturated lactam) and 23 (tricyclic derivative with eight-membered-ring unsaturated lactam) were then obtained from 18 in a number of steps.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier18517171
NPARC number12327995
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Record identifier0034fb7c-bf92-4f55-ac0e-233ee3a5e7e1
Record created2009-09-10
Record modified2016-05-09
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