514-62-5

Usage

Uses

Ferruginol can be used for its antibacterial activities.

InChI:InChI=1/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1

Upstream product

• 10064-25-2 1,2,3,4,4a,9,10,10a-Octahydro-7-isopropenyl-6-methoxy-1,1,4a-trimethylphenanthrene 
• 511-05-7 sugiol 
• 875254-73-2 1-(2-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-yl)-ethanone 
• 141-52-6 sodium ethanolate 
• 22595-42-2 12-methoxy-abieta-8,11,13-trien-19-al semicarbazone 
• 15340-79-1 ferruginol acetate 
• 96888-49-2 C₂₂H₃₂OS₂ 
• 62691-19-4 12-Benzyloxyabieta-8,11,13-trien 
• 24035-66-3 ferruginol benzoate 
• 10064-08-1 (+)-(5S,10S)-12-methoxypodocarpa-8,11,13-triene 
• 10064-28-5 (4aS,10aS)-1,2,3,4,4a,10a-Hexahydro-6-methoxy-1,1,4a-trimethylphenanthrene 
• 19889-20-4 (4aS,10aS)-7-Acetyl-1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy-1,1,4a-trimethylphenanthrene 
• 79593-19-4 (+)-(4aS,10aS)-6-acetyl-7-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene 
• 62691-18-3 12-(benzyloxy)abieta-8,11,13-trien-18-al 

Downstream Products

• 19026-31-4 taxodione 
• 511-05-7 sugiol 
• 24035-66-3 ferruginol benzoate 
• 62751-55-7 8β-Benzoyloxy-12-oxoabieta-9(11),13-dien 
• 62393-73-1 12-benzoyloxy-11-hydroxyabieta-8,11,13-triene 
• 62716-37-4 13α-Benzoyloxy-12-oxoabieta-8(14),9(11)-dien 
• 62691-20-7 13β-Benzoyloxy-12-oxoabieta-8(14),9(11)-dien 
• 640-43-7 ferruginane 
• 37866-99-2 royleanone 
• 62393-78-6 12-Benzoyloxyabieta-8,12-dien-11,14-dion 
• 88664-08-8 (4aS,10aS)-2,3,4,4a,10,10a-hexahydro-5,6-dihydroxy-1,1,4a-trimethyl-7-(1-methylethyl)phenanthren-9(1H)-one 
• 62691-21-8 11-Acetoxy-12-benzoyloxyabieta-8,11,13-trien 
• 62691-22-9 (+)-11-acetoxy-12-benzoyloxy-8,11,13-abietatrien-7-one 
• 120278-22-0 salvinolone 

Relevant academic research and scientific papers

Synthesis of (-)-Chamobtusin A from (+)-Dehydroabietylamine

Chamobtusin A, a unique diterpene alkaloid isolated from Chamaecyparis obtusa cv. tetragon, is considered to be biosynthesized from an abietane diterpenoid. On the basis of this biosynthetic hypothesis, ferruginol (15) was synthesized from (+)-dehydroabietylamine and then biomimetically transformed into (a?)-chamobtusin A in 6 steps (12 steps from (+)-dehydroabietylamine).

Characterization of CYP76AH4 clarifies phenolic diterpenoid biosynthesis in the Lamiaceae

Miltiradiene (1) is the precursor of phenolic diterpenoids such as ferruginol (2), requiring aromatization and hydroxylation. While this has been attributed to a single cytochrome P450 (CYP76AH1), characterization of the rosemary ortholog CYP76AH4 led to the discovery that these CYPs simply hydroxylate the facilely oxidized aromatic intermediate abietatriene (3). The Royal Society of Chemistry 2013.

NEW DITERPENES FROM CHAMAECYPARIS PISIFERA

Three new diterpenes, pisiferin, 15-hydroxyferruginol, and O-methyl pisiferic acid have been isolated and the presence of 12-hydroxyabieta-8,11,13-trien-20-al has been confirmed in studies of the leaves of Chamaecyparis pisifera.The structure of pisiferin, a phenolic diterpene with a new carbon skeleton, has been determined by chemical degradation.The presence of diterpenes of the ferruginol type in the leaves of four varieties of C. pisifera has been examined.- Key Word Index: Chamaecyparis pisifera; Cupressaceae; diterpenes; pisiferin; 15-hydroxyferruginol; O-methyl pisiferic acid; pisiferal.

Bispericyclic Diels–Alder Dimerization of ortho-Quinols in Natural Product (Bio)Synthesis: Bioinspired Chemical 6-Step Synthesis of (+)-Maytenone

Many natural products of plant or microbial origins are derived from enzymatic dearomative oxygenation of 2-alkylphenolic precursors into 6-alkyl-6-hydroxycyclohexa-2,4-dienones. These so-called ortho-quinols cyclodimerize via a remarkably selective bispericyclic Diels–Alder reaction. Whether or not the intervention of catalytic or dirigent proteins is involved during this final step of the biosynthesis of these natural products, this cyclodimerization of ortho-quinols can be chemically reproduced in the laboratory with the same strict level of site-specific regioselectivity and stereoselectivity. This unique yet unified process, which finds its rationale in the inherent chemical reactivity of those ortho-quinols, is illustrated herein by an efficient and bioinspired first chemical synthesis of one of the most structurally complex and synthetically challenging examples of such natural cyclodimers, the bisditerpenoid (+)-maytenone.

Synthesis method of aromatic avaietan diterpenoids

Several methods of synthesizing ferruginol of general formula (1), sugiol of general formula (2) and sugiol methyl ether of general formula (3) have been developed in the prior art, but in order to synthesize the same, there have been probelms that severa

(+/-)-ferruginol analogs and preparation method thereof, and applications of (+/-)-ferruginol analogs in preparation of antibacterial drugs

The present invention discloses (+/-)-ferruginol analogs represented by formulas (I) and (II), and a preparation method thereof, wherein a tricyclic diterpene analog (1) is used as a raw material, andesterification, acylation, oxidation, reduction, dehydroxylation, deprotection, dehydration, halogenation, demethylation and other reactions are performed to obtain the (+/-)-ferruginol analogs represented by the formulas (I) and (II). The invention further discloses a total synthesis method of (+/-)-ferruginol, wherein a compound (16b) as a raw material and a Grignard reagent are subjected to aGrignard reaction, and a dehydroxylation reaction and a demethylation reaction are performed to obtain the (+/-)-ferruginol. According to the present invention, the prepared (+/-)-ferruginol analogs represented by the formulas (I) and (II) have significant antibacterial activity and can be potentially used for the preparation of antibacterial drugs. The formulas (I) and (II) are defined in the specification.

Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes

A sulfenium-ion-initiated, catalytic, enantioselective polyene cyclization is described. Homogeranylarenes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantiomerically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields. The thioether moiety resulting from the reaction can be subsequently transformed into diverse oxygen and carbon functionality postcyclization. The utility of this method is demonstrated by the enantioselective syntheses of (+)-ferruginol and (+)-hinokiol.

Anti-herpetic and anti-dengue activity of abietane ferruginol analogues synthesized from (+)-dehydroabietylamine

The abietane-type diterpenoid (+)-ferruginol (1), a bioactive compound isolated from several plants, has attracted much attention as consequence of its pharmacological properties, which includes antibacterial, antifungal, antimicrobial, cardioprotective, anti-oxidative, anti-plasmodial, leishmanicidal, anti-ulcerogenic, anti-inflammatory and antitumor actions. In this study, we report on the antiviral evaluation of ferruginol (1) and several analogues synthesized from commercial (+)-dehydroabietylamine. Thus, the activity against Human Herpesvirus type 1, Human Herpesvirus type 2 and Dengue Virus type 2, was studied. Two ferruginol analogues showed high antiviral selectivity index and reduced viral plaque-size in post-infection stages against both Herpes and Dengue viruses. A promising lead, compound 8, was ten-fold more potent (EC50 = 1.4 μM) than the control ribavirin against Dengue Virus type 2. Our findings suggest that the 12-hydroxyabieta-8,11,13-triene skeleton, which is characteristic of the diterpenoid ferruginol (1), is an interesting molecular scaffold for development of novel antivirals. In addition, the cytotoxic and antifungal activities of the synthesized ferruginol analogues have also been investigated.

Antimalarial activity of abietane ferruginol analogues possessing a phthalimide group

The abietane-type diterpenoid (+)-ferruginol, a bioactive compound isolated from New Zealand's Miro tree (Podocarpus ferruginea), displays relevant pharmacological properties, including antimicrobial, cardioprotective, anti-oxidative, anti-plasmodial, leishmanicidal, anti-ulcerogenic, anti-inflammatory and anticancer. Herein, we demonstrate that ferruginol (1) and some phthalimide containing analogues 2-12 have potential antimalarial activity. The compounds were evaluated against malaria strains 3D7 and K1, and cytotoxicity was measured against a mammalian cell line panel. A promising lead, compound 3, showed potent activity with an EC50 = 86 nM (3D7 strain), 201 nM (K1 strain) and low cytotoxicity in mammalian cells (SI > 290). Some structure-activity relationships have been identified for the antimalarial activity in these abietane analogues.

Syntheses of taiwaniaquinone F and taiwaniaquinol A via an unusual remote C-H functionalization

A protecting-group-free route to (-)-taiwaniaquinone F based on a ring contraction and subsequent aromatic oxidation of a sugiol derivative is reported. In addition, the first synthesis of (+)-taiwaniaquinol A is reported via short time exposure of (-)-taiwaniaquinone F to sunlight triggering a remote C-H functionalization. The hypothesis that the biogenesis of some methylenedioxy bridged natural products could proceed via similar nonenzymatic mechanisms is presented.