Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates

Organic Letters
Thomas E NielsenMorten Meldal

Abstract

A general strategy for the solid-phase synthesis of structurally diverse bicyclic dipeptide mimetics is presented. Depending on the amino acid side-chain (R(1)), peptide-derived N-acyliminium intermediates may undergo nucleophilic attack from either side-chain functional groups (-OH, -NH(2), -SH, and -CONH(2)) or the amide backbone (-CONH-) of the peptide, thus affording a range of aza-, thia-, and oxabicycloalkanes in excellent purity and diastereoselectivity. [reaction: see text]

References

Feb 8, 2002·Journal of Peptide Science : an Official Publication of the European Peptide Society·Albert Loffet
Apr 12, 2003·Science·Robert L Strausberg, Stuart L Schreiber
May 22, 2004·The Journal of Organic Chemistry·Thomas E Nielsen, Morten Meldal

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Citations

Dec 18, 2012·ACS Combinatorial Science·Agustina La VeniaViktor Krchňák
Dec 11, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Paula GomesRui Moreira
Apr 19, 2016·Chemical Communications : Chem Comm·Alhosna BenjdiaOlivier Berteau
Dec 15, 2007·Angewandte Chemie·Thomas E Nielsen, Stuart L Schreiber
Mar 13, 2010·Biopolymers·Sebastian T Le QuementThomas E Nielsen
Nov 25, 2011·Organic & Biomolecular Chemistry·Milovan StojanovićMarija Baranac-Stojanović
Oct 30, 2016·Angewandte Chemie·Dong-Chao WangShu-Li You
Jul 26, 2012·Angewandte Chemie·Dimitris KalaitzakisGeorgios Vassilikogiannakis
Oct 5, 2011·Organic & Biomolecular Chemistry·Mark DowAdam Nelson
May 8, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Vanesa Giménez-Navarro, Viktor Krchňák
Jan 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrea CalcaterraFrancesca Ghirga
Jul 5, 2007·Organic & Biomolecular Chemistry·Masood HosseiniJanne E Tønder
Jan 28, 2009·The Journal of Organic Chemistry·Stijn DekeukeleireNorbert De Kimpe
Oct 10, 2008·The Journal of Organic Chemistry·José Luis García RuanoCristina Fajardo
Jul 9, 2009·Organic Letters·Christian Bukovec, Uli Kazmaier
Nov 13, 2007·Journal of Combinatorial Chemistry·Sebastian T Le QuementMorten Meldal
Jun 8, 2021·Frontiers in Chemistry·Yunliang ChenWei Ding
Aug 19, 2021·Drug Metabolism Reviews·Siva Nageswara Rao GajulaRajesh Sonti
Nov 2, 2017·The Journal of Organic Chemistry·Alessia BertaminoIsabel M Gomez-Monterrey

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