55623-34-2

Upstream product

• 3484-53-5 <1R-(1α,4aβ,4bα,6α,10aα)>-1,2,3,4,4a,4b,5,6,10,10a-Decahydro-6-hydroxy-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrencarbonsaeure-methylester 
• 108-24-7 acetic anhydride 
• 67-68-5 dimethyl sulfoxide 
• 928819-29-8 methyl 12α-chloroabietate 
• 928819-28-7 C₂₃H₃₆O₅ 
• 82652-60-6 methyl 13α,14α-dihydroxyabiet-7-en-19-oate 
• 514-10-3 (?)-abietic acid 
• 127-25-3 abietic acid methyl ester 
• 3484-53-5 (1R,4aR,6S)-6-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid methyl ester 
• 3787-85-7 methyl 8α-hydroxy-12-oxo-13-abietan-18-oate 
• 5309-31-9 methyl 8,12α-epidioxy-13-abietan-18-oate 

Downstream Products

• 13742-23-9 (1R,4aS,10aR)-6-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester 
• 13742-23-9 (1R,4aS)-6-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester 
• 30906-06-0 Methyl-12-acetoxydehydroabietat 
• 22595-48-8 18-Hydroxyferruginol 

Relevant academic research and scientific papers

Synthesis of 4- epi-Parviflorons A, C, and E: Structure-Activity Relationship Study of Antiproliferative Abietane Derivatives

The first syntheses of 4-epi-parviflorons A, C, and E (4-epi-1-3) were achieved in 12-13 steps from commercially available (-)-abietic acid (5). All synthesized compounds, including intermediates and derivatives, were evaluated for antiproliferative activity against five human tumor cell lines. A structure-activity relationship study revealed no significant difference between Pf E and 4-epi-Pf E, the importance of two oxygen functional groups at C-11 and C-12 for antiproliferative activity, as well as a combination of carbomethoxy at C-4 and a benzoyl ester with electron-drawing group at C-12 or hydroxymethyl at C-4 and an appropriate oxidation state of ring-B/C for triple-negative breast cancer cell selectivity.

First synthesis of picealactone C. A new route toward taxodione-related terpenoids from abietic acid

A new route to 12-hydroxyabietic acid (10) and related compounds from abietic acid (12), via acetoxyalcohol 15, is reported. Utilizing this, the first synthesis of picealactone C (5) was achieved. The synthesis of natural 12-hydroxydehydroabietic acid (8), 18-hydroxyferruginol (9) and methyl 12α-hydroxyabietate (11) is also reported.

ENDOPEROXIDE DITERPENOIDS AND OTHER CONSTITUENTS FROM ABIES MAROCANA

From the acid fraction of the hexane extract of the needles of Abies marocana three endperoxide diterpenoids, methyl 12α-hydroxyabietate and a triterpenoid, in addition to other resin acids have been isolated.

Synthesis of (+)-Taxodione

A stereoselective synthesis of (+)-taxodione (1) starting from (-)-abietic acid (2) via the ironcarbonyl complex 4 is described.Conversion of the carboxyl function of 4 into a methyl group via 5 and 6 proceeds in excellent overall yield.The next steps are the introduction of oxygen functions in the positions 12 and 6.Oxidation with BSA yields the quinonemethide 1.The 1H- and 13C-NMR resonances of all compounds have been assigned.