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

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Standard

Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates. / Nielsen, Thomas E.; Le Quement, Sebastian; Meldal, Morten.

I: Organic Letters, Bind 7, Nr. 17, 18.08.2005, s. 3601-3604.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Nielsen, TE, Le Quement, S & Meldal, M 2005, 'Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates', Organic Letters, bind 7, nr. 17, s. 3601-3604. https://doi.org/10.1021/ol050871j

APA

Nielsen, T. E., Le Quement, S., & Meldal, M. (2005). Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates. Organic Letters, 7(17), 3601-3604. https://doi.org/10.1021/ol050871j

Vancouver

Nielsen TE, Le Quement S, Meldal M. Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates. Organic Letters. 2005 aug. 18;7(17):3601-3604. https://doi.org/10.1021/ol050871j

Author

Nielsen, Thomas E. ; Le Quement, Sebastian ; Meldal, Morten. / Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates. I: Organic Letters. 2005 ; Bind 7, Nr. 17. s. 3601-3604.

Bibtex

@article{4e1605d9498b4c9891751e02cc85ee51,
title = "Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates",
abstract = "(Chemical Equation Presented) A general strategy for the solid-phase synthesis of structurally diverse bicyclic dipeptide mimetics is presented. Depending on the amino acid side-chain (R1), peptide-derived N-acyliminium intermediates may undergo nucleophilic attack from either side-chain functional groups (-OH, -NH2, -SH, and -CONH2) or the amide backbone (-CONH-) of the peptide, thus affording a range of aza-, thia-, and oxabicycloalkanes in excellent purity and diastereoselectivity.",
author = "Nielsen, {Thomas E.} and {Le Quement}, Sebastian and Morten Meldal",
year = "2005",
month = aug,
day = "18",
doi = "10.1021/ol050871j",
language = "English",
volume = "7",
pages = "3601--3604",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "17",

}

RIS

TY - JOUR

T1 - Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates

AU - Nielsen, Thomas E.

AU - Le Quement, Sebastian

AU - Meldal, Morten

PY - 2005/8/18

Y1 - 2005/8/18

N2 - (Chemical Equation Presented) A general strategy for the solid-phase synthesis of structurally diverse bicyclic dipeptide mimetics is presented. Depending on the amino acid side-chain (R1), peptide-derived N-acyliminium intermediates may undergo nucleophilic attack from either side-chain functional groups (-OH, -NH2, -SH, and -CONH2) or the amide backbone (-CONH-) of the peptide, thus affording a range of aza-, thia-, and oxabicycloalkanes in excellent purity and diastereoselectivity.

AB - (Chemical Equation Presented) A general strategy for the solid-phase synthesis of structurally diverse bicyclic dipeptide mimetics is presented. Depending on the amino acid side-chain (R1), peptide-derived N-acyliminium intermediates may undergo nucleophilic attack from either side-chain functional groups (-OH, -NH2, -SH, and -CONH2) or the amide backbone (-CONH-) of the peptide, thus affording a range of aza-, thia-, and oxabicycloalkanes in excellent purity and diastereoselectivity.

U2 - 10.1021/ol050871j

DO - 10.1021/ol050871j

M3 - Journal article

C2 - 16092829

AN - SCOPUS:24044449622

VL - 7

SP - 3601

EP - 3604

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 17

ER -

ID: 326847053