10219-81-5

Upstream product

• 38818-83-6 12-methoxyabieta-8,11,13-trien-6-one 
• 19889-21-5 1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone 
• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 106-24-1 Geraniol 
• 38011-83-5 trans-1-(4,8-dimethylnona-3,7-dien-1-yl)-4-methoxybenzene 
• 10064-08-1 1,2,3,4,4a,9,10,10a-Octahydro-6-methoxy-1,1,4a-trimethylphenanthrene 
• 2162-53-0 sugiol acetate 
• 15340-79-1 (+/-)-ferruginol acetate 
• 514-62-5 (+/-)-ferruginol 
• 10064-10-5 6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-ol 
• 64217-00-1 (+/-)-xanthopherol methyl ether 
• 38818-83-6 (cis)-4b,6,7,8,8a,10-hexahydro-2-isopropyl-3-methoxy-4b,8,8-trimethyl-9(5H)-phenanthrenone 
• 64158-64-1 (+/-)-6-Acetoxy-12-methoxy-abieta-5,8,11,13-tetraen-7-on 
• 105401-95-4 3-isopropyl-4-methoxy-benzoic acid methyl ester 

Downstream Products

• 514-62-5 (+/-)-ferruginol 

Relevant academic research and scientific papers

(+/-)-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.

Synthesis of C-7 oxidized abietane diterpenes from racemic ferruginyl methyl ether

A series of naturally occurring C-7 oxidized abietane diterpenes have been synthesized from racemic ferruginyl methyl ether in high yields. 6-Hydroxyl-5,6-dehydrosugiol (7) can be converted into stable xanthoperol (12) using high temperature. Among the products, the structures of sugiyl methyl ether (2) and 6(-hydroxysugiyl methyl ether (8) were determined by X-ray analysis.

Total Synthesis of (+/-)-12-Methoxyabieta-8,11,13-trien-6-one, a Versatile Intermediate for Diterpene Synthesis

The title compound (1) has been synthesized from perhydro-4α-methoxy-5,5,8a-trimethylnaphthalen-1-one (12).The formyl derivative (14) was subjected to Robinson annelation with 4-diethylaminobutan-2-one methiodide to obtain the adduct (15) and this, on heating with sodium methoxide in methanol, yielded the tricyclic ketone (16).The enolate of (16), generated by treatment with lithium di-isopropylamide, reacted with acetone in the presence of anhydrous zinc chloride to afford an aldol (21) which, on heating with toluene-p-sulphonic acid in benzene, provided the dienone (22); subsequent treatment with sulphuric acid in methanol produced the dimethoxyabietatriene (6) whose conversion into the desired ketone (1) was accomplished by treatment with trichloromethylsilane and sodium iodide followed by oxidation of the resulting compound with Jones' reagent and then methylation with dimethylsulphate and alkali.Elimination of C-6 carbonyl group of the ketone (1) and subsequent oxidation with chromium trioxide and acetic acid yielded the ketone (3) which, on demethoxylation with silicon tetrachloride and sodium iodide, yielded sugiol (2).