Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D

R. Alan Aitken; Lorna Murray

doi:10.1016/j.tetlet.2017.09.073

Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D

R. Alan Aitken, Lorna Murray

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Abstract

Six stabilised phosphonium ylides bearing ortho-benzylaminophenyl and cinnamoyl (or a heterocyclic analogue) groups have been prepared and upon flash vacuum pyrolysis at 800 °C were found to undergo cascade cyclization processes to give mainly 3-styrylquinolines but also in some cases ring-fused carbazoles and other fused-ring heterocyclic products. By starting with an appropriate ring-methylated precursor the natural product Eustifoline D was obtained in 19% yield in the pyrolysis in addition to the 3-(2-furylethenyl)quinoline (46%).

Original language	English
Pages (from-to)	4328-4332
Number of pages	5
Journal	Tetrahedron Letters
Volume	58
Issue number	46
Early online date	27 Sept 2017
DOIs	https://doi.org/10.1016/j.tetlet.2017.09.073
Publication status	Published - 15 Nov 2017

Keywords

Cyclization
Gas-phase reaction
Phosphorus ylides
Fused-ring systems
Radical reaction

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10.1016/j.tetlet.2017.09.073

17TL Aitken&Murray rev
© 2017 Elsevier Ltd. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.tetlet.2017.09.073
Accepted author manuscript, 421 KBLicence: CC BY-NC-ND

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title = "Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D",

abstract = "Six stabilised phosphonium ylides bearing ortho-benzylaminophenyl and cinnamoyl (or a heterocyclic analogue) groups have been prepared and upon flash vacuum pyrolysis at 800 °C were found to undergo cascade cyclization processes to give mainly 3-styrylquinolines but also in some cases ring-fused carbazoles and other fused-ring heterocyclic products. By starting with an appropriate ring-methylated precursor the natural product Eustifoline D was obtained in 19% yield in the pyrolysis in addition to the 3-(2-furylethenyl)quinoline (46%).",

keywords = "Cyclization, Gas-phase reaction, Phosphorus ylides, Fused-ring systems, Radical reaction",

author = "Aitken, {R. Alan} and Lorna Murray",

note = "The authors thank EPSRC (UK) for a DTA studentship (Grant No. EP/P501768/1).",

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doi = "10.1016/j.tetlet.2017.09.073",

language = "English",

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T1 - Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D

AU - Aitken, R. Alan

AU - Murray, Lorna

N1 - The authors thank EPSRC (UK) for a DTA studentship (Grant No. EP/P501768/1).

PY - 2017/11/15

Y1 - 2017/11/15

N2 - Six stabilised phosphonium ylides bearing ortho-benzylaminophenyl and cinnamoyl (or a heterocyclic analogue) groups have been prepared and upon flash vacuum pyrolysis at 800 °C were found to undergo cascade cyclization processes to give mainly 3-styrylquinolines but also in some cases ring-fused carbazoles and other fused-ring heterocyclic products. By starting with an appropriate ring-methylated precursor the natural product Eustifoline D was obtained in 19% yield in the pyrolysis in addition to the 3-(2-furylethenyl)quinoline (46%).

AB - Six stabilised phosphonium ylides bearing ortho-benzylaminophenyl and cinnamoyl (or a heterocyclic analogue) groups have been prepared and upon flash vacuum pyrolysis at 800 °C were found to undergo cascade cyclization processes to give mainly 3-styrylquinolines but also in some cases ring-fused carbazoles and other fused-ring heterocyclic products. By starting with an appropriate ring-methylated precursor the natural product Eustifoline D was obtained in 19% yield in the pyrolysis in addition to the 3-(2-furylethenyl)quinoline (46%).

KW - Cyclization

KW - Gas-phase reaction

KW - Phosphorus ylides

KW - Fused-ring systems

KW - Radical reaction

U2 - 10.1016/j.tetlet.2017.09.073

DO - 10.1016/j.tetlet.2017.09.073

M3 - Article

SN - 0040-4039

VL - 58

SP - 4328

EP - 4332

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D

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