Phthalides from

Naito, T., T. Katsuhara, K. Niitsu, Y. Ikeya, M. Okada, and H. Mitsuhashi. 1992. Two phthalides from Ligusticum chuangxiong. Phytochemistry 31 639-642. 

Fischer et al. (1991) have applied a highspeed counter-current chromatography with an Ito multi-layer coil separator-extractor to perform efficient separations of aromarelevant constituents, such as phthalides, from celery and parsley roots. 

Zheng G-Q, Kenney PM, Zhang J, et al. 1993. Chemoprevention of benzo[a]pyrene-induced forestomach cancer in mice by natural phthalides from celery seed oil. Nutr Cancer 19 77-86. 

Scheme 3.42 Synthesis of phthalides from benzimidates and aldehydes.

Scheme 3.43 Synthesis of phthalides from benzoic acids and aldehydes.

Fig. 102. Separation of some phthalides from coumarin. Layer silica gel GF254 detection fluorescence quenching in short wave UV light [258]. 1 phthalide 2 coumarin 3 isobutylidene-3a, 4-dihydrophthalide 4 phenylphthalide 5 butyl-phthalide 6 benzalphthalide 7 ligustilide blue fluorescence in 365 nm light 8 butylidene phthalide. G mixture 1—8...

Scheme 2.161 Pd-catalyzed carbonylative synthesis of phthalides from 2-bromo benzaldehydes.

Pyrolysis of a-alkoxyenolesters Phthalides from o-oxocarboxylic acid esters... 

Alvarenga M A et al. (21 authors) 1978 Dihydroisocoumarins and phthalide from wood samples infested by fungi. Phytochemistry 17 511-516... 

Inouye H, Okuda T, Hirata Y, Nagakura N, Yoshizaki M 1967 Structure of catalpalactone, a new phthalide from catalpa wood. Chem Pharm Bull 15 786-792... 

Sodium boron hydride sodium hydrogen carbonate Phthalides from o-aldehydocarboxylic acids s. 12, 111... 

Hydrocarbons from ketones Selective reduction s. 13,112 Phthalides from o-dicarboxylic acid anhydrides s. 11,123... 

Phthalides from carboxylic acid amides via o-substitution... 

A direct formation of y-lactone 17 through benzylic oxidation of aryl carboxylic acid 16 using a hypervalent iodine(III) reagent 18 and KBr was presented by Dohi and Kita [16] (Scheme 7). This reaction was successfully applied to the synthesis of phthalides from o-alkyl benzoic acids. 

Moreover, they are versatile building blocks for the synthesis of functionalized naphthalenes, anthracenes, and naphthacene natural products [8]. Recently, Rh-catalyzed C-H activation followed by nucleophilic addition to aldehydes emerged as a powerful alternative to access phthalides. In 2012, Li and coworkers developed a novel Rh(III)-catalyzed synthesis of three substituted phthalides from benzoic acids and aldehydes through carboxylate-directed ortho-C-H functionalization and subsequent intramolecular cyclization (Scheme 6.2a) [9]. In 2013, GooCen and coworkers described the straightforward synthesis of S-alkylidenephthalides from benzoic acids and aliphatic acids or anhydrides in the presence of [Rh(cod)Cl]2 and CsF (Scheme 6.2b) [10]. 

Scheme 6.2 (a) Synthesis of 3-substituted phthalides from aldehydes and aromatic acids and (b) synthesis of 3-alkylidenephthalides from benzoic acids. 

SCHEME 5.54 Rh-catalyzed cascade synthesis of phthalides from phthalaldehyde and aryl-boronic acids. 

Intramolecular photochemical Cannizzaro reaction Phthalides from phthalaldehydes... 

---