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

Thomas E. Nielsen; Sebastian Le Quement; Morten Meldal

doi:10.1021/ol050871j

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

Thomas E. Nielsen, Sebastian Le Quement, Morten Meldal^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › Research › peer-review

53 Citations (Scopus)

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.

Original language	English
Journal	Organic Letters
Volume	7
Issue number	17
Pages (from-to)	3601-3604
Number of pages	4
ISSN	1523-7060
DOIs	https://doi.org/10.1021/ol050871j
Publication status	Published - 18 Aug 2005
Externally published	Yes

Access to Document

10.1021/ol050871j

Cite this

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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,

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doi = "10.1021/ol050871j",

language = "English",

volume = "7",

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journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

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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

SN - 1523-7060

VL - 7

SP - 3601

EP - 3604

JO - Organic Letters

JF - Organic Letters

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ER -