1991-28-2

Usage

InChI:InChI=1/C13H10O4/c1-6-5-8-9(15)3-4-10(16)12(8)13(17)11(6)7(2)14/h3-5,17H,1-2H3

Upstream product

• 120016-62-8 5-acetoxy-6-acetyl-7-methylnaphthalene-1,4-dione 
• 115061-31-9 methyl 4,8-diacetoxy-5-methoxynaphthalene-2-carboxylate 
• 120016-61-7 Acetic acid 2-acetyl-5,8-dimethoxy-3-methyl-naphthalen-1-yl ester 
• 120016-58-2 methyl 4-hydroxy-5,8-dimethoxynaphthalene-2-carboxylate 
• 120016-57-1 4,8-Dihydroxy-5-methoxy-naphthalene-2-carboxylic acid methyl ester 
• 120016-60-6 1-(1-hydroxy-5,8-dimethoxy-3-methylnaphthalen-2-yl)ethanone 
• 120016-59-3 3-(hydroxymethyl)-5,8-dimethoxynaphthalen-1-ol 
• 95636-27-4 5,8-dimethoxy-3-methylnaphthalen-1-yl acetate 
• 50559-08-5 5,8-dimethoxy-3-methylnaphthalen-1-ol 
• 69945-29-5 5,8-Diacetoxy-2-acetyl-6,7-dibrom-4-chlor-3-methyl-1-naphthol 
• 69945-30-8 5,8-Diacetoxy-2-acetyl-4-chlor-3-methyl-1-naphthol 

Relevant academic research and scientific papers

The Synthesis of Stypandrol, a Toxic Binaphthalenetetrol Isolated from Stypandra imbiricata: New Syntheses of Dianellidin and Stypandrone

New syntheses of the naphthalenoid natural products dianellidin (2) and stypandrone (20), which rely on the Fries rearrangement, are described.This methodology is then applied to the synthesis of stypandrol (1), a toxic naphthalenetetrol isolated from Stypandra imbiricata R.Br. ('blind grass').

Dimeric Naphthoquinones, 17. Synthesis of Stypandrone and Dianellinone

The naphthoquinone stypandrone (2b) ist synthesized via the intermediates 5a, 6a and 6b.Selective monoalkylation of its hydroquinone yields the monoether 12b, which, on phenol oxidation and oxidative dealkylation, leads to 13 and dianellinone (2a).The synthesis confirms the 3,3'-dimerisation of the natural product. - Keywords: Naphthoquinones, Stypandrone, Dianellinone, Phenol Oxidation