13161-32-5Relevant articles and documents
A Biomimetic Synthesis of des -Hydroxy Paecilospirone
Feng, Zhen-Gao,Burnett, G. Leslie,Pettus, Thomas R. R.
supporting information, p. 1517 - 1519 (2018/05/16)
The carbon framework of des -hydroxy paecilospirone was rapidly synthesized using a biomimetic approach whereby an enol ether and an ortho -quinone methide (o- QM), each derived from the same lactone, were combined to arrive at the complete carbon skeleton of paecilospirone.
Total synthesis of neo-tanshinlactones through a cascade benzannulation-lactonization as the key step
Ghosh, Ketaki,Karmakar, Raju,Mal, Dipakranjan
, p. 4037 - 4046 (2013/07/19)
The cascade annulation-lactonization of phthalides with α-carboxyfurylacrylates in the presence of lithium hexamethyldisilazide (LiHMDS) provides both convergent and semiconvergent regioselective syntheses of neo-tanshinlactones in moderate yields. This methodology also offers an avenue for the direct syntheses of hitherto unreported 6-alkoxycarbonyl-substituted neo-tanshinlactones and their heterocyclic analogues. A new synthesis of 4-alkyl phthalides was developed on the basis of a combination of a Duff reaction and Fuerstner cross-coupling. The cascade benzannulation-lactonization of phthalides with α-carboxyfurylacrylates was employed as the key reaction for the concise synthesis of neo-tanshinlactone. Copyright
Regiocontrolled rearrangement of isobenzofurans
Egan, Ben A.,Paradowski, Michael,Thomas, Lynne H.,Marquez, Rodolfo
supporting information; experimental part, p. 2086 - 2089 (2011/06/25)
Regioselective alkylation and oxidative rearrangement of isobenzofurans has been achieved to generate substituted 4,8- ihydroxyisochromanones in good yields and with complete regiocontrol.
7-Hydroxyphthalide: A new natural salicylaldehyde analog from Oulenzia sp. (Astigmata: Winterschmitiidae)
Shimizu, Nobuhiro,Kuwahara, Yasumasa
, p. 990 - 992 (2007/10/03)
A new salicyl lactone was detected from the unidentified Oulenzia sp. and its chemical structure was elucidated as 7-hydroxyphthalide (7-hydroxy-3H-isobenzofuran-1-one), based on its GC/MS and GC/FT-IR data and SiO2 column behavior. The compound was synthesized by NaBH4 reduction of 3-hydroxyphthalic anhydride. The GC/MS and GC/FT-IR spectra of the natural compound were consistent with those of the synthetic product. Although the compound is known as a medical material, this is the first example of its presence in nature.
Facile Interconversion of the Isomeric Acid Chlorides Derived from Half Methyl Esters of 3-Methoxyphthalic Acid
Gupta, Dahmendra N.,Hodge, Philip,Hurley, Peter N.
, p. 391 - 394 (2007/10/02)
The isomeric acid chlorides obtained by treating the half methyl esters of 3-methoxyphthalic acid with thionyl chloride interconvert so readily that it is not practical to isolate one acid chloride free of the other.At equilibrium the main isomer is the a
A New Route to 4-Hydroxytetralones and 1-Naphthols
Broom, Nigel J. P.,Sammes, Peter G.
, p. 465 - 470 (2007/10/02)
The lithium salts, derived from position 3 of phthalides by treatment with hindered bases, participate in Michael addition reactions with a variety of conjugated olefins.For singly activated olefins the conjugate anion reacts intramolecularly with the lactone group to produce 4-hydroxytetralones in moderate to good yield.Dehydration of these hydroxytetralones, by brief treatment with acid, produces the corresponding α-naphthol.Substituted phthalides react similarly making the method a general one for the production of substituted α-naphthols.
