Total synthesis of tyrosine-derived tetramic acid pigments from a slime mould

Nassima Riache; Christine Bailly; Alexandre Deville; Lionel Dubost; Bastien Nay

doi:10.1002/ejoc.201000597

Total synthesis of tyrosine-derived tetramic acid pigments from a slime mould

Nassima Riache, Christine Bailly, Alexandre Deville, Lionel Dubost, Bastien Nay

CNRS/Museum National d'Histoire Naturelle/IRD/UPMC

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

Abstract

A method for the total synthesis of naturally occurring 3-enoyltetramic acids derived from L-tyrosine is described, allowing for three chemical transformations to occur in one pot by using a multicomponent mixture, The sequence involves (1) a base-promoted Lacey-Dieckmann condensation, (2) a Michaelis-Becker reaction, and (3) a Wittig-Horner-Emmons reaction between the resulting 3-phosphonoacetyltetramic acid and an appropriate aldehyde. This sequence of reactions was applied to the synthesis of polyenic pigments obtained from the slime mould Leocarpus fragilis starting from readily available precursors. A series of structurally related compounds was also synthesized and their antibiotic significance was evaluated to elucidate their role in nature.

Original language	English
Pages (from-to)	5402-5408
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	28
DOIs	https://doi.org/10.1002/ejoc.201000597
Publication status	Published - 1 Oct 2010
Externally published	Yes

Keywords

Antibiotics
Dyes/pigments
Multicomponent reactions
Total synthesis
Wittig reactions

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10.1002/ejoc.201000597

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title = "Total synthesis of tyrosine-derived tetramic acid pigments from a slime mould",

abstract = "A method for the total synthesis of naturally occurring 3-enoyltetramic acids derived from L-tyrosine is described, allowing for three chemical transformations to occur in one pot by using a multicomponent mixture, The sequence involves (1) a base-promoted Lacey-Dieckmann condensation, (2) a Michaelis-Becker reaction, and (3) a Wittig-Horner-Emmons reaction between the resulting 3-phosphonoacetyltetramic acid and an appropriate aldehyde. This sequence of reactions was applied to the synthesis of polyenic pigments obtained from the slime mould Leocarpus fragilis starting from readily available precursors. A series of structurally related compounds was also synthesized and their antibiotic significance was evaluated to elucidate their role in nature.",

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T1 - Total synthesis of tyrosine-derived tetramic acid pigments from a slime mould

AU - Riache, Nassima

AU - Bailly, Christine

AU - Deville, Alexandre

AU - Dubost, Lionel

AU - Nay, Bastien

PY - 2010/10/1

Y1 - 2010/10/1

N2 - A method for the total synthesis of naturally occurring 3-enoyltetramic acids derived from L-tyrosine is described, allowing for three chemical transformations to occur in one pot by using a multicomponent mixture, The sequence involves (1) a base-promoted Lacey-Dieckmann condensation, (2) a Michaelis-Becker reaction, and (3) a Wittig-Horner-Emmons reaction between the resulting 3-phosphonoacetyltetramic acid and an appropriate aldehyde. This sequence of reactions was applied to the synthesis of polyenic pigments obtained from the slime mould Leocarpus fragilis starting from readily available precursors. A series of structurally related compounds was also synthesized and their antibiotic significance was evaluated to elucidate their role in nature.

AB - A method for the total synthesis of naturally occurring 3-enoyltetramic acids derived from L-tyrosine is described, allowing for three chemical transformations to occur in one pot by using a multicomponent mixture, The sequence involves (1) a base-promoted Lacey-Dieckmann condensation, (2) a Michaelis-Becker reaction, and (3) a Wittig-Horner-Emmons reaction between the resulting 3-phosphonoacetyltetramic acid and an appropriate aldehyde. This sequence of reactions was applied to the synthesis of polyenic pigments obtained from the slime mould Leocarpus fragilis starting from readily available precursors. A series of structurally related compounds was also synthesized and their antibiotic significance was evaluated to elucidate their role in nature.

KW - Antibiotics

KW - Dyes/pigments

KW - Multicomponent reactions

KW - Total synthesis

KW - Wittig reactions

U2 - 10.1002/ejoc.201000597

DO - 10.1002/ejoc.201000597

M3 - Article

AN - SCOPUS:77957128139

SN - 1434-193X

SP - 5402

EP - 5408

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 28

ER -

Total synthesis of tyrosine-derived tetramic acid pigments from a slime mould

Abstract

Keywords

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