Synthese des Maclurin‐pentamethyläthers

Kostanecki, v.; Tambor, J.

doi:10.1002/cber.19060390486

Cited by 22 publications

(4 citation statements)

References 3 publications

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“…Our synthesis of lamellarin G trimethyl ether ( 3 ) began with two commercially available precursors, homoveratrylamine ( 8 ) and homoveratric acid ( 9 ). Both can be made in several steps from vanillin, − a common xylochemical derived from lignin by hydrothermal depolymerization or electrolysis . Their condensation to form the amide 10 was accomplished in the absence of solvent in a slight modification of a reported procedure by heating equimolar quantities of the reactants at 180 °C in a closed microwave vessel at a power setting of 150 W for 1 h (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

A Xylochemically Inspired Synthesis of Lamellarin G Trimethyl Ether via an Enaminone Intermediate

et al. 2019

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A concise high yielding synthesis of lamellarin G trimethyl ether has been achieved from precursors and solvents that can in principle be derived from xylochemical (woody biomass) sources. The route is comparatively green in that some reactions are performed without solvent or with relatively benign solvents. In addition, chromatographic purification of products is avoided, and only a single aqueous workup is performed. The novelty of the synthesis lies in the intermediacy of an enaminone for the construction of the central pyrrole ring. The overall yield of the product is among the highest reported to date.

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Section: Resultsmentioning

confidence: 99%

A Xylochemically Inspired Synthesis of Lamellarin G Trimethyl Ether via an Enaminone Intermediate

et al. 2019

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“…The known 3,3Ј,4,4Ј-tetramethoxybenzophenone (11) [34] was obtained according to the procedure published by Kulkarni et al [34c] from 3,4-dimethoxybenzoic acid (9) and veratrole (10) in polyphosphoric acid (PPA) in 77% yield (Scheme 3). Surprisingly, subsequent reduction of 11, according to various known procedures, was unsuccessful.…”

Section: Synthesis Of 23671011-hexamethoxytribenzotriquinacene (3)mentioning

confidence: 99%

2,3,6,7,10,11‐Hexamethoxytribenzotriquinacene: Synthesis, Solid‐State Structure, and Functionalization of a Rigid Analogue of Cyclotriveratrylene

et al. 2004

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The syntheses of several tribenzotriquinacenes bearing six methoxy groups at the outer peripheral positions of the aromatic rings are reported. The centro‐methyl derivative is accessible in surprisingly good yield through two‐fold cyclodehydration in the final step of a synthesis route which requires special care in the preparation of some electron‐rich key intermediates, such as 5,6‐dimethoxy‐2‐methylindane‐1,3‐dione and bis(3,4‐dimethoxyphenyl)methanol. X‐ray single‐crystal structure analysis of the centro‐methyl derivative confirms its C3v‐symmetrical molecular structure but, at variance from the parent centro‐methyltribenzotriquinacene and the similarly shaped cyclotriveratrylene, the hexamethoxytribenzotriquinacene analog does not form columnar stacks in the solid state. Functionalization of the three benzhydrylic bridgehead positions leads to the tetramethyl analog and the bridgehead triol in good yields. In contrast, attempts to functionalize the ortho positions by nitration or bromination mainly give rise to ring cleavage through electrophilic ipso attack, which parallels the behavior of cyclotribenzylenes and cyclotriveratrylenes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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“…460) was prepared by the Reimer-Tiemann reaction (Johnson & Stevenson, 1936); veratric acid (m.p. 1810) was prepared in a similar manner (Kostanecki & Tambor, 1906). For feeding, the aldehyde was melted in warm water and the acid was neutralized with Na2CO3 solution.…”

Section: Methods and Resultsmentioning

confidence: 99%