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

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...

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Bibliographic Details
Published in:Organic letters 2019-08, Vol.21 (16), p.6295-6299
Main Authors: Sheng, Bingbing, Vo, Yen, Lan, Ping, Gardiner, Michael G, Banwell, Martin G, Sun, Pinghua
Format: Article
Language:English
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Summary: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 discussed.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02172