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A Short Total Synthesis of (±)-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction

Monaco, A; Szulc, BR; Rao, ZX; Barniol-Xicota, M; Sehailia, M; Borges, BMA; Hilton, ST; (2017) A Short Total Synthesis of (±)-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction. Chemistry: A European Journal , 23 (20) pp. 4750-4755. 10.1002/chem.201700143. Green open access

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Abstract

An intramolecular acylal cyclisation (IAC) approach to the synthesis of a range of bicyclic heterocycles is reported. As an example of the utility of the IAC reaction, the methodology was applied in a protecting-group free five-step total synthesis of (±)-lycorane, incorporating a novel intramolecular Heck addition reaction to generate the pentacyclic core structure of the natural product in good yield.

Type: Article
Title: A Short Total Synthesis of (±)-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/chem.201700143
Publisher version: http://dx.doi.org/10.1002/chem.201700143
Language: English
Additional information: This is the peer reviewed version of the following article: Monaco, A., Szulc, B. R., Rao, Z. X., Barniol-Xicota, M., Sehailia, M., Borges, B. and Hilton, S. (2017), A Short Total Synthesis of (±)-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction. Chem. Eur. J.. Accepted Author Manuscript. doi:10.1002/chem.201700143, which has been published in final form at http://dx.doi.org/10.1002/chem.201700143. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
UCL classification: UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > Div of Biosciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > Div of Biosciences > Neuro, Physiology and Pharmacology
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > SoP Pharmaceutical and Bio Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/1542248
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