2001
DOI: 10.1055/s-2001-15147
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New Palladium-Catalysed Access to 3-(1'-Indanylidene) Phthalide, Precursor of the Core of Fredericamycin A

Abstract: An efficient synthesis of 3-(1'-indanilydene) phthalide is described via a palladium-catalysed biscyclisation step.

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Cited by 17 publications
(7 citation statements)
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“…Finally, we examined an intramolecular carbometalation reaction17 starting from the readily available alkynyl iodide 6 (Scheme ) 18. The treatment of 6 with i Pr 2 Zn (0.55 equiv) in the presence of Li(acac) (10 mol %) in NMP at 25 °C for 12 h provided the desired diaryl zinc reagent, which underwent a smooth carbocupration in the presence of CuCN⋅2 LiCl13 (1.1 equiv) to give the copper reagent 7 stereoselectively.…”
Section: Methodsmentioning
confidence: 99%
“…Finally, we examined an intramolecular carbometalation reaction17 starting from the readily available alkynyl iodide 6 (Scheme ) 18. The treatment of 6 with i Pr 2 Zn (0.55 equiv) in the presence of Li(acac) (10 mol %) in NMP at 25 °C for 12 h provided the desired diaryl zinc reagent, which underwent a smooth carbocupration in the presence of CuCN⋅2 LiCl13 (1.1 equiv) to give the copper reagent 7 stereoselectively.…”
Section: Methodsmentioning
confidence: 99%
“…Abschließend untersuchten wir ausgehend vom leicht zugänglichen Alkinyliodid 6 17 eine intramolekulare Carbometallierung (Schema ) 18. Die Reaktion mit i Pr 2 Zn (0.55 Äquiv.)…”
Section: Methodsunclassified
“…One of them was developed on pentynoic acids 3-substituted with an halogeno-aryl moiety such as 22 [25][26]. Using these conditions, the expected lactone 28 was obtained in 64% yield along with 10% of the isocoumarin 29 which was easily removed by recrystallization [28]. The reaction took place at room temperature in DMSO, in the presence of t-BuOK as base and Pd(OAc)2 / tri(2-furyl)phosphine as catalytic system.…”
Section: / Cyclizations Involving Organopalladium Complexes As Electmentioning
confidence: 99%