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 | Zendy

Bingbing Sheng | Zendy; Yen Vo | Zendy; Ping Lan | Zendy; Michael G. Gardiner | Zendy; Martin G. Banwell | Zendy; PingHua Sun | Zendy

Open Access

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

Author(s) -

Bingbing Sheng,

Yen Vo,

Ping Lan,

Michael G. Gardiner,

Martin G. Banwell,

PingHua Sun

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b02172

Subject(s) - phthalide , chemistry , catalysis , metal , stereochemistry , combinatorial chemistry , organic chemistry

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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research