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Modular Synthesis and Biological Investigation of 5-Hydroxymethyl Dibenzyl Butyrolactones and Related Lignans

School of Chemical Sciences, University of Auckland, Aucklamd 1010, New Zealand
School of Healthcare Science, Manchester Metropolitan University, Manchester M1 5GD, UK
The MacDiarmid Institute for Advanced Materials and Nanotechnology, Wellington 6140, New Zealand
Author to whom correspondence should be addressed.
Molecules 2018, 23(12), 3057;
Received: 12 November 2018 / Revised: 20 November 2018 / Accepted: 21 November 2018 / Published: 22 November 2018
(This article belongs to the Special Issue Lignans)
PDF [1800 KB, uploaded 28 November 2018]


Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway. View Full-Text
Keywords: lignans; dibenzyl butyrolactones; anti-proliferative; acyl-Claisen; stereoselective synthesis lignans; dibenzyl butyrolactones; anti-proliferative; acyl-Claisen; stereoselective synthesis

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Davidson, S.J.; Pilkington, L.I.; Dempsey-Hibbert, N.C.; El-Mohtadi, M.; Tang, S.; Wainwright, T.; Whitehead, K.A.; Barker, D. Modular Synthesis and Biological Investigation of 5-Hydroxymethyl Dibenzyl Butyrolactones and Related Lignans. Molecules 2018, 23, 3057.

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