Cart
Article
Amino Acid Derived Heterocycles: Lewis Acid Catalyzed and Radical Cyclizations from Peptide Acetals
Full Text HTML
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
Bicyclization of peptide acetals via nucleophilic attack of a phenyl group on an endocyclic acyliminium ion 4 was explored as a route to novel amino acid derived heterocycles and peptidomimetic scaffolds. In the presence of protic acid, bridged structures such as 6 are formed readily from phenylalanine derivatives, but the fused-ring analogues 5 could not be obtained in good yield. In contrast, radical cyclization of the bromophenyl dihydropyrazinone 7 provides an effective alternative for the synthesis of 5 (n = 0, 1, 2). Additional versatility in this process was demonstrated by efficient synthesis of a different fused ring system, represented by the antihelmintic praziquantel, 8.
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 7 ACS Journal articles (5 most recent appear below).
Practical Solid-Phase Parallel Synthesis of Δ5-2-Oxopiperazines via N-Acyliminium Ion Cyclization
Sung-Chan Lee and Seung Bum ParkJournal of Combinatorial Chemistry2007 9 (5), 828-835Practical Solid-Phase Parallel Synthesis of Δ5-2-Oxopiperazines via N-Acyliminium Ion Cyclization
Sung-Chan Lee and Seung Bum ParkJournal of Combinatorial Chemistry2007 9 (5), 828-835A practical solid-phase strategy for the synthesis of Δ5-2-oxopiperazines via N-acyliminium ion cyclization has been developed. A key step in the library synthesis is tandem acidolytic cleavage with subsequent in situ iminium formation, followed by stable ...
The Synthetic Versatility of Acyloxyborohydrides
Gordon W. GribbleOrganic Process Research & Development2006 10 (5), 1062-1075The Synthetic Versatility of Acyloxyborohydrides
Gordon W. GribbleOrganic Process Research & Development2006 10 (5), 1062-1075Acyloxyborohydrides are unsurpassed in their versatility as reagents in organic synthesis. In addition to their superior ability in effecting reductive amination of aldehydes and ketones, acyloxyborohydrides can reduce nitrogen heterocycles (indoles, ...
Regioselective Unusual Formation of Spirocyclic 4-{2‘-Benzo(2‘,3‘-dihydro)furo}- 9-methyl-2,3,9-trihydrothiopyrano[2,3-b]indole by 4-exo-trig Aryl Radical Cyclization and Rearrangement
K. C. Majumdar and S. AlamOrganic Letters2006 8 (18), 4059-4062Regioselective Unusual Formation of Spirocyclic 4-{2‘-Benzo(2‘,3‘-dihydro)furo}- 9-methyl-2,3,9-trihydrothiopyrano[2,3-b]indole by 4-exo-trig Aryl Radical Cyclization and Rearrangement
K. C. Majumdar and S. AlamOrganic Letters2006 8 (18), 4059-40624-(2‘-Bromoaryloxymethylene)-9-methyl-2,3,9-trihydrothiopyrano[2,3-b]indoles under tri-n-butyltin hydride mediated aryl radical cyclization furnished exclusively the 4-{2‘-benzo(2‘,3‘-dihydro)furo}-9-methyl-2,3,9-trihydrothiopyrano[2,3-b]indoles in ...
Virtual Hydrocarbon and Combinatorial Databases for Use with CAVEAT
Yongliang Yang, Dmitri V. Nesterenko, Ryan P. Trump, Ken Yamaguchi, Paul A. Bartlett, and Dale G. DrueckhammerJournal of Chemical Information and Modeling2005 45 (6), 1820-1823Virtual Hydrocarbon and Combinatorial Databases for Use with CAVEAT
Yongliang Yang, Dmitri V. Nesterenko, Ryan P. Trump, Ken Yamaguchi, Paul A. Bartlett, and Dale G. DrueckhammerJournal of Chemical Information and Modeling2005 45 (6), 1820-1823Three new virtual databases have been developed for use with the bond-orientation-based database searching program CAVEAT. These consist of a database of trisubstituted monocyclic hydrocarbons having ethyl, vinyl, and phenyl substituents; a database of ...
Cyclizations of N-Acyliminium Ions
Bruce E. Maryanoff, Han-Cheng Zhang, Judith H. Cohen, Ignatius J. Turchi, and Cynthia A. MaryanoffChemical Reviews2004 104 (3), 1431-1628Cyclizations of N-Acyliminium Ions
Bruce E. Maryanoff, Han-Cheng Zhang, Judith H. Cohen, Ignatius J. Turchi, and Cynthia A. MaryanoffChemical Reviews2004 104 (3), 1431-1628
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue June 14, 2002
- Received October 10, 2001
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
