- Synthesis of 4- epi-Parviflorons A, C, and E: Structure-Activity Relationship Study of Antiproliferative Abietane Derivatives
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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.
- Miyajima, Yui,Saito, Yohei,Takeya, Munehisa,Goto, Masuo,Nakagawa-Goto, Kyoko
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- First synthesis of picealactone C. A new route toward taxodione-related terpenoids from abietic acid
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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.
- Alvarez-Manzaneda, Enrique,Chahboun, Rachid,Cabrera, Eduardo,Alvarez, Esteban,Alvarez-Manzaneda, Ramón,Lachkar, Mohammed,Messouri, Ibtissam
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p. 989 - 992
(2008/02/04)
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- ENDOPEROXIDE DITERPENOIDS AND OTHER CONSTITUENTS FROM ABIES MAROCANA
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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.
- Barrero, Alejandro F.,Sanchez, Juan F.,Alvarez-Manzaneda, E. J.,Dorado, M. Munoz,Haidour, Ali
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p. 593 - 597
(2007/10/02)
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- Synthesis of (+)-Taxodione
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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.
- Haslinger, Ernst,Michl, Guenter
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p. 677 - 686
(2007/10/02)
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