Products of an Acetylation Protocol on Two Pentaalkoxynaphthalenes

Giles, Robin G. F.; Green, Ivan R.; Eeden, Nester van

doi:10.1080/00397910600616693

Cited by 5 publications

(2 citation statements)

References 13 publications

(18 reference statements)

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“…: 44 °C (nhexane). 35 36 [4-(Benzyloxy)-3-bromo-5-methoxyphenyl]methanol (13). Sodium borohydride (10.2 g, 270 mmol, 1.5 equiv) is dissolved in ethanol (300 mL), and 4-(benzyloxy)-3-bromo-5-methoxybenzaldehyde (57.9 g, 180 mmol, 1.0 equiv) dissolved in ethanol (200 mL) is added dropwise at 0 °C.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine

2017

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Two consecutive Cu-catalyzed Ullmann-type C-O couplings permitted the first successful entry toward the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine

2017

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“…O-benzyl-3-bromovanillin 3 was readily prepared in 97% yield following a reported protocol 6 starting from commercially available 3-bromovanillin (5) (Scheme2). With these starting materials in hand, we next turned our attention to the coupling reaction focusing on coppermediated conditions.…”

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confidence: 99%

Unexpected copper mediated benzyl O→O migration during an Ullmann ether coupling

Vanucci-Bacqué¹,

Chaabouni²,

Fabing³

et al. 2014

Tetrahedron Letters

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The synthesis of a highly functionalized phenolic diaryl ether 5,5'-oxybis(4-hydroxy-3methoxybenzaldehyde) (1) potentially interesting as new scaffold for drug design, has been carried out using Ullmann coupling conditions. An unusual benzyl migration in obenzyloxyphenol moiety occurred during this reaction leading to an unexpected compound identified as 4-(benzyloxy)-3-(2-(benzyloxy)-4-formyl-6-methoxyphenoxy)-5-methoxy benzaldehyde (7). A rationale for this migration process is proposed.

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