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

Bingbing Sheng; Yen Vo; Ping Lan; Michael G. Gardiner; Martin G. Banwell; Pinghua Sun

doi:10.1021/acs.orglett.9b02172

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

Bingbing Sheng, Yen Vo, Ping Lan, Michael G. Gardiner, Martin G. Banwell^*, Pinghua Sun

^*Corresponding author for this work

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18 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	6295-6299
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.9b02172
Publication status	Published - 16 Aug 2019

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title = "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",

abstract = "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.",

author = "Bingbing Sheng and Yen Vo and Ping Lan and Gardiner, {Michael G.} and Banwell, {Martin G.} and Pinghua Sun",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = aug,

day = "16",

doi = "10.1021/acs.orglett.9b02172",

language = "English",

volume = "21",

pages = "6295--6299",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "16",

}

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; Lan, Ping et al.
In: Organic Letters, Vol. 21, No. 16, 16.08.2019, p. 6295-6299.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Direct and Metal-Catalyzed Photochemical Dimerization of the Phthalide (Z)-Ligustilide Leading to Both [2 + 2] and [4 + 2] Cycloadducts

T2 - Application to Total Syntheses of Tokinolides A-C and Riligustilide

AU - Sheng, Bingbing

AU - Vo, Yen

AU - Lan, Ping

AU - Gardiner, Michael G.

AU - Banwell, Martin G.

AU - Sun, Pinghua

PY - 2019/8/16

Y1 - 2019/8/16

N2 - 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.

AB - 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.

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DO - 10.1021/acs.orglett.9b02172

M3 - Article

SN - 1523-7060

VL - 21

SP - 6295

EP - 6299

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

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

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