Synthesis of new diverse macrocycles from diol precursors

Charlotte Marie Madsen; Martin Hansen; Marie V. Thrane; Mads Hartvig Clausen

doi:10.1016/j.tet.2010.10.071

Synthesis of new diverse macrocycles from diol precursors

Charlotte Marie Madsen, Martin Hansen, Marie V. Thrane, Mads Hartvig Clausen

Department of Chemistry

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

Abstract

The formation of a library of diverse macrocycles with different ring sizes from two easily accessible building blocks is presented. Reacting diol precursors with electrophilic reagents lead to 17-membered sulfites and 19-membered malonates in 34–79% yield. Double-reductive amination of dialdehyde analogs of the diol precursors leads to 15-membered amines in yields ranging from 9 to 60%, reflecting large differences in reactivity based on steric environment.

Original language	English
Journal	Tetrahedron
Volume	66
Issue number	52
Pages (from-to)	9849-9859
ISSN	0040-4020
DOIs	https://doi.org/10.1016/j.tet.2010.10.071
Publication status	Published - 2010

Keywords

Macrocyclization
Reductive amination
Diversity-oriented synthesis
Cyclic esters

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title = "Synthesis of new diverse macrocycles from diol precursors",

abstract = "The formation of a library of diverse macrocycles with different ring sizes from two easily accessible building blocks is presented. Reacting diol precursors with electrophilic reagents lead to 17-membered sulfites and 19-membered malonates in 34–79% yield. Double-reductive amination of dialdehyde analogs of the diol precursors leads to 15-membered amines in yields ranging from 9 to 60%, reflecting large differences in reactivity based on steric environment.",

keywords = "Macrocyclization, Reductive amination, Diversity-oriented synthesis, Cyclic esters",

author = "Madsen, {Charlotte Marie} and Martin Hansen and Thrane, {Marie V.} and Clausen, {Mads Hartvig}",

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journal = "Tetrahedron",

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T1 - Synthesis of new diverse macrocycles from diol precursors

AU - Madsen, Charlotte Marie

AU - Hansen, Martin

AU - Thrane, Marie V.

AU - Clausen, Mads Hartvig

PY - 2010

Y1 - 2010

N2 - The formation of a library of diverse macrocycles with different ring sizes from two easily accessible building blocks is presented. Reacting diol precursors with electrophilic reagents lead to 17-membered sulfites and 19-membered malonates in 34–79% yield. Double-reductive amination of dialdehyde analogs of the diol precursors leads to 15-membered amines in yields ranging from 9 to 60%, reflecting large differences in reactivity based on steric environment.

AB - The formation of a library of diverse macrocycles with different ring sizes from two easily accessible building blocks is presented. Reacting diol precursors with electrophilic reagents lead to 17-membered sulfites and 19-membered malonates in 34–79% yield. Double-reductive amination of dialdehyde analogs of the diol precursors leads to 15-membered amines in yields ranging from 9 to 60%, reflecting large differences in reactivity based on steric environment.

KW - Macrocyclization

KW - Reductive amination

KW - Diversity-oriented synthesis

KW - Cyclic esters

U2 - 10.1016/j.tet.2010.10.071

DO - 10.1016/j.tet.2010.10.071

M3 - Journal article

VL - 66

SP - 9849

EP - 9859

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 52

ER -