85178-50-3

Basic information

• Product Name: Tetrangulol methyl ether
• Synonyms: 1-Hydroxy-8-methoxy-3-methylbenz[a]anthracene-7,12-dione;Antibiotic X-14881E;Tetrangulol methyl ether;X-14881E
• CAS NO: 85178-50-3
• Molecular Formula: C20H14O4
• Molecular Weight: 318.32276
• Mol File: 85178-50-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Tetrangulol methyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrangulol methyl ether(85178-50-3)
• EPA Substance Registry System: Tetrangulol methyl ether(85178-50-3)

Safety Data

• Hazardous Substances Data: 85178-50-3(Hazardous Substances Data)

Upstream product

• 7414-92-8 Tetrangulol 
• 77-78-1 dimethyl sulfate 
• 131919-12-5 8-O-methyltetrangomycin 
• 56630-78-5 (+/-)-rubiginone B₂ 
• 81418-42-0 3-acetyl-5-methoxy-1,4-naphthoquinone 
• 179949-47-4 6-hydroxy-8-methoxy-3-methyl-1-oxo-2,4-dihydrobenzanthracen-7,12-dione 
• 326803-15-0 trifluoro-methanesulfonic acid 8-methoxy-3-methyl-1,7,12-trioxo-1,2,3,4,7,12-hexahydro-benzo[a]anthracen-6-yl ester 
• 202195-07-1 3-methoxy-5-methyl-2-(1,4,5-trimethoxynaphthalen-2-yl)benzaldehyde 
• 7414-94-0 1,8-dimethoxy-3-methylbenz[a]anthracene-7,12-dione 
• 69833-09-6 2-bromo-5-methoxy-[1,4]naphthoquinone 
• 869487-91-2 3-allyl-2-bromo-5-methoxynaphthalene-1,4-dione 
• 69008-03-3 2-bromo-5-hydroxy-[1,4]naphthoquinone 
• 149402-07-3 3-allyl-2-bromo-1,4,5-trimethoxynaphthalene 
• 169128-02-3 3-Dimethylfluorosilanyl-8-methoxy-3-methyl-1,2,3,4-tetrahydrobenzanthracene-7,12-dione 

Downstream Products

• 7414-92-8 Tetrangulol 

Relevant articles and documents

Reactions of [2-(2-Naphthyl)phenyl]acetylenes and 2-(2-Naphthyl)benzaldehyde O-Phenyloximes: Synthesis of the Angucycline Tetrangulol and 1,10,12-Trimethoxy-8-methylbenzo[c]phenanthridine

The Suzuki–Miyaura coupling reaction between (1,4,5-trimethoxynaphthalen-2-yl)boronic acid and 2-iodo-3-methoxy-5-methylbenzaldehyde gave the intermediate 3-methoxy-5-methyl-2-(1,4,5-trimethoxynaphthalen-2-yl)benzaldehyde. Conversion of this benzaldehyde

A unified strategy for the syntheses of angucyclinone antibiotics: Total syntheses of tetrangulol, kanglemycin M, X-14881-E, and anhydrolandomycinone

A unified strategy for the syntheses of angucyclinone antibiotics was developed utilizing sequential intramolecular enyne metathesis, Diels-Alder/aromatization, photooxygenation, and one-pot elimination/ aromatization reactions. The diversity in this sequ

A general approach to angucyclines: Synthesis of hatomarubigin A, rubiginone B2, antibiotic X-1488E, 6-hydroxytetrangulol, and tetrangulol

Hatomarubigin A was prepared in 41% yield in a single procedure from acyl naphthoquinone 15 and 5-methylcyclohexane-1,3-dione (16). The net reaction consists of Michael addition to an acyl quinone followed by intramolecular aldol condensation. Hatomarubigin A then served as a common intermediate in syntheses of the angucyclinone antibiotics rubiginone B2, antibiotic X-1488E, 6-hydroxytetrangulol, and tetrangulol. (C) 2000 Elsevier Science Ltd.

Synthesis of Naturally (MM 47755; X-14881 E) and Non-Naturally Occuring Aromatic Angucyclinones

The Diels-Alder reactions of the naphthoquinones 1-4 with the dienes 5a-7 were investigated.The regioisomeric outcome of the adducts 10a-10g, 16, and 23 is in agreement with theoretical predictions from frontier orbital calculations.The adduct 10a was further converted to the non-natural (e.g. 15) and the adduct 16 to the natural angucyclinones MM 47755 (19a) and X-14881 E (22) by silicon-oxygen exchange and photooxygenation.The addition of naphthoquinones 2 and 4 to dienes 6 and 7 afford the Diels-Alder adducts 16 and 23, respectively, which are valuable intermediates for further transformation into non-aromatic angucyclinones. - Keywords: Angucyclinones / MM 47755 / X-14881 E / Diels-Alder reactions / Silicon-oxygen exchange