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Direct and Metal-Catalyzed Photochemical Dimerization of the Phthalide (Z)-Ligustilide Leading to Both [2 + 2] and [4 + 2] Cycloadducts: Application to Total Syntheses of Tokinolides A-C and Riligustilide

Sheng, Bingbing; VO, Yen Thi-Hoang; Lan, Ping; Gardiner, Michael; Banwell, Martin; Sun, Pinghua


Synthetically derived (Z)-ligustilide (1) has been subjected to photochemically-promoted dimerization processes under a range of conditions. By such means, varying distributions of the dimeric natural products tokinolides A-C (4, 3, and 6, respectively) and riligustilide (5) as well certain related (isomeric) compounds have been obtained. The structures of three of them have been confirmed by single-crystal X-ray analysis. The biosynthetic implications of the outcomes of this study are...[Show more]

CollectionsANU Research Publications
Date published: 2019
Type: Journal article
Source: Organic Letters
DOI: 10.1021/acs.orglett.9b02172


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