Site-Selective Mono-Oxidation of 1,2-Bis(boronates)
Site-selective oxidation of vicinal bis(boronates) is accomplished through the use of trimethylamine N-oxide in 1-butanol solvent. The reaction occurs with good efficiency and selectivity across a range of substrates, providing 2-hydro-1-boronic esters which are shown to be versatile intermediates in the synthesis of chiral building blocks.
Yan, Lu,Morken, James P.
supporting information
p. 3760 - 3763
(2019/05/24)
Modular synthesis and biological investigation of 5-hydroxymethyl dibenzyl butyrolactones and related 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.
Davidson, Samuel J.,Pilkington, Lisa I.,Dempsey-Hibbert, Nina C.,El-Mohtadi, Mohamed,Tang, Shiying,Wainwright, Thomas,Whitehead, Kathryn A.,Barker, David
(2018/11/30)
LITHIATION OF THE BENZENE RING IN THE PRESENCE OF ortho-ALKYL SUBSTITUENTS BEARING ONE OR TWO HETEROATOMS ON THE β-CARBON. A CONVENIENT SYNTHESIS OF MELLEIN AND KIGELIN
The title reaction can be successfully accomplished by proton-metal exchange with n-butyllithium, and the usually observed elimination to a styrene derivative suppressed, provided an appropriate combination of heteroatoms bound to the β-carbon of the alky
Napolitano, Elio,Morsani, Massimo,Fiaschi, Rita
p. 249 - 255
(2007/10/02)
Synthetic Studies on the Cyclopropyl Iminium Ion Rearrangement. 3. Application of the Cyclopropyl Acyliminium Ion Rearrangement to a Concise and Highly Convergent Synthesis of (+/-)-Lycorine
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Boeckman, Robert K.,Goldstein, Steven W.,Walters, Michael A.
p. 8250 - 8252
(2007/10/02)
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