N-Fmoc-dehydroalanine: A versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids

Brendan A. Burkett; Christina L.L. Chai

doi:10.1016/S0040-4039(00)01113-8

N-Fmoc-dehydroalanine: A versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids

Brendan A. Burkett, Christina L.L. Chai^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	6661-6664
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4039(00)01113-8
Publication status	Published - 19 Aug 2000

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abstract = "The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed. (C) 2000 Elsevier Science Ltd.",

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T2 - A versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids

AU - Burkett, Brendan A.

AU - Chai, Christina L.L.

PY - 2000/8/19

Y1 - 2000/8/19

N2 - The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed. (C) 2000 Elsevier Science Ltd.

AB - The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed. (C) 2000 Elsevier Science Ltd.

KW - Dehydroalanine

KW - Diels-Alder reactions

KW - Solid-phase synthesis

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U2 - 10.1016/S0040-4039(00)01113-8

DO - 10.1016/S0040-4039(00)01113-8

M3 - Article

SN - 0040-4039

VL - 41

SP - 6661

EP - 6664

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

N-Fmoc-dehydroalanine: A versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids

Abstract

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