Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D
MetadataShow full item record
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%).
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
© 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
DescriptionThe authors thank EPSRC (UK) for a DTA studentship (Grant No. EP/P501768/1).
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.