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