The Synthesis of Ventilone A

Matthew Piggott, Dieter Wege

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

2-Amino-3,6-dimethoxy-4,5-methylenedioxybenzoic acid (12) was prepared from 1,4-dimethoxy-2,3-methylenedioxybenzene (8) via the isatin (11). The benzyne generated from (12) was intercepted with 3-acetyl-2-ethoxy-4[(4-methoxyphenoxy)methyl] furan (4) to give the naphthol (27), which on treatment with ceric ammonium nitrate gave the dimethyl ether of ventilone A (29). Demethylation with boron tribromide then afforded ventilone A (1).
Original languageEnglish
Pages (from-to)749-754
JournalAustralian Journal of Chemistry
Volume53
Issue number2000
DOIs
Publication statusPublished - 2000

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Isatin
Naphthols
Boron
Acids
dimethyl ether
furan
benzyne
ceric ammonium nitrate
1,3-benzodioxole

Cite this

Piggott, Matthew ; Wege, Dieter. / The Synthesis of Ventilone A. In: Australian Journal of Chemistry. 2000 ; Vol. 53, No. 2000. pp. 749-754.
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The Synthesis of Ventilone A. / Piggott, Matthew; Wege, Dieter.

In: Australian Journal of Chemistry, Vol. 53, No. 2000, 2000, p. 749-754.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The Synthesis of Ventilone A

AU - Piggott, Matthew

AU - Wege, Dieter

PY - 2000

Y1 - 2000

N2 - 2-Amino-3,6-dimethoxy-4,5-methylenedioxybenzoic acid (12) was prepared from 1,4-dimethoxy-2,3-methylenedioxybenzene (8) via the isatin (11). The benzyne generated from (12) was intercepted with 3-acetyl-2-ethoxy-4[(4-methoxyphenoxy)methyl] furan (4) to give the naphthol (27), which on treatment with ceric ammonium nitrate gave the dimethyl ether of ventilone A (29). Demethylation with boron tribromide then afforded ventilone A (1).

AB - 2-Amino-3,6-dimethoxy-4,5-methylenedioxybenzoic acid (12) was prepared from 1,4-dimethoxy-2,3-methylenedioxybenzene (8) via the isatin (11). The benzyne generated from (12) was intercepted with 3-acetyl-2-ethoxy-4[(4-methoxyphenoxy)methyl] furan (4) to give the naphthol (27), which on treatment with ceric ammonium nitrate gave the dimethyl ether of ventilone A (29). Demethylation with boron tribromide then afforded ventilone A (1).

U2 - 10.1071/CH00057

DO - 10.1071/CH00057

M3 - Article

VL - 53

SP - 749

EP - 754

JO - Australian Journal of Chemistry:an international journal for chemical science

JF - Australian Journal of Chemistry:an international journal for chemical science

SN - 0004-9425

IS - 2000

ER -