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%).
Citation
Aitken , R A & Murray , L 2017 , ' Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D ' , Tetrahedron Letters , vol. 58 , no. 46 , pp. 4328-4332 . https://doi.org/10.1016/j.tetlet.2017.09.073
Publication
Tetrahedron Letters
Status
Peer reviewed
ISSN
0040-4039Type
Journal article
Rights
© 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
Description
The authors thank EPSRC (UK) for a DTA studentship (Grant No. EP/P501768/1).Collections
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