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Developing neolignans as proangiogenic agents: Stereoselective total syntheses and preliminary biological evaluations of the four guaiacylglycerol 8-O-4'-coniferyl ethers

Buckler, Joshua; Banwell, Martin; Kordbacheh, Farzaneh; Parish, Christopher; Santiago, Fernando; Khachigian, Levon M


Stereoselective total syntheses of the four stereoisomeric forms of guaiacylglycerol 8-O-4′-coniferyl ether, viz., compounds 1, ent- 1, 2, and ent- 2, have been established. The key step involves an Evans/Seebach auxiliarycontrolled and syn-selective aldol process followed, in the reaction sequences leading to the anti-compounds, by a Mitsunobu reaction involving a benzylic alcohol residue. The proangiogenic properties of the synthetic materials were evaluated in a human microvascular...[Show more]

CollectionsANU Research Publications
Date published: 2017
Type: Journal article
Source: ACS Omega
DOI: 10.1021/acsomega.7b01459
Access Rights: Open Access


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