- Stereoselective synthesis of (Z)-3-ylidenephthalides via AlCl3-mediated cyclization with 2-acylbenzoic acids
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An efficient method for the synthesis of (Z)-3-ylidenephthalides is reported in moderate to high yield with AlCl3 as catalyst. Different substrates of the 2-acylbenzoic acids are well performed in the Z/E selectivity. This method is highlighted
- Feng, Ziming,Jiang, Jianshuang,Li, Gangsheng,Wang, Xujie,Yang, Yanan,Zhang, Peicheng,Zhang, Xu
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- Regioselective synthesis of natural and unnatural (Z)-3-(1- alkylidene)phthalides and 3-substituted isocoumarins starting from methyl 2- hydroxybenzoates
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(Z)-3-(1-Alkylidene)phthalides and 3-substituted isocoumarins, which include compounds bearing a substituent on their benzene ring, have been selectively and efficiently synthesized by a new protocol which involves: (i) the conversion of methyl 2-hydroxybenzoates into the corresponding nonaflates; (ii) Pd-catalyzed alkynylation reactions of these derivatives; (iii) the conversion of the so obtained methyl 2-(1-alkynyl)benzoates into the corresponding carboxylic acids followed by a transition metal-catalyzed heteroannulation reaction. This procedure has been used to prepare either natural products such as senkyunolide B, senkyunolide C, 3-propylisocoumarin and artemidin, or the MEM-ether of senkyunolide E. The regioselectivity of the transition metal-catalyzed cyclization reactions of 2-(1-alkynyl)benzoic acids has proven to be affected either by the catalyst used or the type of 1- alkynyl group present in these carboxylic acids. (C) 2000 Elsevier Science Ltd.
- Bellina, Fabio,Ciucci, Donatella,Vergamini, Piergiorgio,Rossi, Renzo
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p. 2533 - 2545
(2007/10/03)
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- A convenient approach for synthesis of (Z)-3-butylidenephthalide derivatives
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The reaction of n-BuLi with phthalic anhydride derivatives leads to (Z)-3-butylidenephthalide derivatives.
- Li, Shaobai,Wang, Zhiwci,Fang, Xiaoping,Yang, Yating,Li, Yulin
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p. 1783 - 1791
(2007/10/03)
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- Efficient Synthesis of Hydroxyphthalides
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Naturally occurring hydroxyphthalides were synthesized via migration of double bond regio- and stereoselectively.Isomerization of E-isomer to Z-isomer easily occurred under acidic or basic conditions.
- Ogawa, Yoshimitsu,Maruno, Masao,Wakamatsu, Takeshi
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