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Open AccessArticle

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

1
School of Chemical Sciences, University of Auckland, Aucklamd 1010, New Zealand
2
School of Healthcare Science, Manchester Metropolitan University, Manchester M1 5GD, UK
3
The MacDiarmid Institute for Advanced Materials and Nanotechnology, Wellington 6140, New Zealand
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(12), 3057; https://doi.org/10.3390/molecules23123057
Received: 12 November 2018 / Revised: 20 November 2018 / Accepted: 21 November 2018 / Published: 22 November 2018
(This article belongs to the Special Issue Lignans)
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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