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Journal articles on the topic 'Podocarpic acid'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Cambie, RC, PS Rutledge, and PD Woodgate. "Transformations of Podocarpic Acid." Australian Journal of Chemistry 46, no. 10 (1993): 1447. http://dx.doi.org/10.1071/ch9931447.

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The A and C rings of the aromatic diterpenoid resin acid podocarpic acid from the heartshakes of the New Zealand conifer Dacrydium cupressinum have been modified to provide useful chiral intermediates for synthesis. The various strategies used by the Auckland group are reviewed.

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2

Cambie, RC, PA Craw, DK Murray, et al. "Dimers of Podocarpic Acid Derivatives." Australian Journal of Chemistry 49, no. 1 (1996): 167. http://dx.doi.org/10.1071/ch9960167.

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Treatment of methyl 12-hydroxypodocarpa-8,11,13-trien-19-oate (5) with a commercial sample of thallium(III) trifluoroacetate gave a low yield (5%) of a non-symmetric ether-linked dimer (15). Use of freshly prepared thallium(III) trifluoroacetate gave a 28% yield of the symmetrical biaryl dimer (16). The dimethyl ether (17) was prepared in low yield (10%) by treatment of methyl 12-methoxypodocarpa-8,11,13-trien-19-oate (4) with the latter reagent.

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3

Cambie, RC, AC Grimsdale, PS Rutledge, and PD Woodgate. "Syntheses of Confertifolin, Winterin and Isodrimenin Congeners From Podocarpic Acid." Australian Journal of Chemistry 43, no. 3 (1990): 485. http://dx.doi.org/10.1071/ch9900485.

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Podocarpic acid (11) has been converted into the congener (5) of confertifolin (4) through the o-quinone (29) formed by oxidations of the catechol monoether (15) and the 13-amine (16) with Fremy's salt. Oxidation of the methyl ether (12) afforded the p- quinone (44) which was converted into the congener (6) of winterin (7). Podocarpic acid has also been converted into the congener (8) of isodrimenin (9) through the catechol derivative (37).

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4

Bendall, JG, RC Cambie, AC Grimsdale, PS Rutledge, and PD Woodgate. "Synthesis of Winterin From Podocarpic Acid." Australian Journal of Chemistry 45, no. 6 (1992): 1063. http://dx.doi.org/10.1071/ch9921063.

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Ozonolysis of a hydroquinone derived from podocarpic acid (1) gave the biologically active natural product winterin (11). Treatment of the quinone (12) with ozone gave a ring-contracted spiro furanone, the mechanism of formation of which is proposed.

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5

Cambie, RC, PI Higgs, PS Rutledge, and PD Woodgate. "Aryne Chemistry of Podocarpic Acid Derivatives." Australian Journal of Chemistry 47, no. 8 (1994): 1483. http://dx.doi.org/10.1071/ch9941483.

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The anthranilic acid (2), a key intermediate for the generation of an aryne at C13 of podocarpic acid derivatives, was synthesized from the 14-amino compound (5) which in turn was generated regiospecifically in high yield by treatment of the 13-bromo compound (25) with sodamide in liquid ammonia. The amine was converted into the anthranilic acid by two separate routes: firstly by directed lithiation and trapping of the lithium species with a CO2 moiety, and secondly by oxidative cleavage of an isatin fused across positions 13 and 14.

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6

Cambie, Richard C., Perry K. Davy, Lorna H. Mitchell, Clifton E. F. Rickard, and Peter S. Rutledge. "Oxidative Decarboxylation of Podocarpic Acid Derivatives." Australian Journal of Chemistry 51, no. 8 (1998): 653. http://dx.doi.org/10.1071/c97213.

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The radical decarboxylation–sulfoxide cycloelimination of 2′-pyridylthio esters formed from a series of podocarpic acid derivatives gives Δ4(18) -alkenes in high yield. An exception is the 13-nitro acid (2) which affords a thiohydroxamic ester (28), the relative stability of which is attributed to inhibition of the radical chain reaction by the nitro group. The stereochemistry of the pyridyl sulfide (18) has been confirmed by X-ray crystallography.

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7

Cambie, Richard C., Michael R. Metzler, Peter S. Rutledge, and Paul D. Woodgate. "Organoiron complexes of podocarpic acid derivatives." Journal of Organometallic Chemistry 398, no. 1-2 (1990): 117–31. http://dx.doi.org/10.1016/0022-328x(90)87009-3.

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8

Cambie, Richard C., Michael R. Metzler, Clifton E. F. Rickard, Peter S. Rutledge, and Paul D. Woodgate. "Organomanganese complexes of podocarpic acid derivatives." Journal of Organometallic Chemistry 425, no. 1-2 (1992): 59–87. http://dx.doi.org/10.1016/0022-328x(92)80023-q.

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9

Cambie, RC, MR Metzler, PS Rutledge, and PD Woodgate. "Synthesis of Benzannulated Derivatives of Podocarpic Acid." Australian Journal of Chemistry 44, no. 10 (1991): 1383. http://dx.doi.org/10.1071/ch9911383.

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10

Burnell, Robert H., Michel Jean, and Sonia Marceau. "Synthesis of maytenoquinone." Canadian Journal of Chemistry 66, no. 2 (1988): 227–30. http://dx.doi.org/10.1139/v88-037.

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11

Cambie, RC, MP Hay, L. Larsen, CEF Rickard, PS Rutledge, and PD Woodgate. "Ring A Modifications of Podocarpic Acid: Towards the Synthesis of Quassinoids." Australian Journal of Chemistry 44, no. 6 (1991): 821. http://dx.doi.org/10.1071/ch9910821.

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Efficient methods for the formation of the hydroxy enone moieties in (17), (18), (45) and (46) from podocarpic acid (1) have been developed. The exocyclic alkene (13) has been converted into the α-hydroxy enones (17) and (18) in six steps and high overall yield. Oxidation of the enones (7) and (44) with manganese(III) acetate gave high yields of the α-acetoxy enones (10) and (47) and (48), respectively. Hydrolysis of (10), (47) and (48) afforded the α-hydroxy enones (11), (45) and (46), respectively. Hydroboration-oxidation of the alkene mixture (38) and (41) provided the alcohol (53) (53%) wh

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12

Cambie, Richard C., Clifton E. F. Rickard, and Gary A. Strange. "Utilization of Podocarpic Acid for Nagilactone Synthesis." Australian Journal of Chemistry 50, no. 8 (1997): 841. http://dx.doi.org/10.1071/c96198.

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Methods for constructing the C-ring of nagilactones from the ring C ozonolysis products of methyl podocarpate have been investigated. The stereochemistry of an aldol adduct (15) and the structure of a dihydropyridazinone derivative (17) have been confirmed by X-ray crystallography.

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13

Wolff, Robert L. "All-cis 5,11,14-20:3 acid: Podocarpic acid or sciadonic acid?" Journal of the American Oil Chemists' Society 76, no. 10 (1999): 1255–56. http://dx.doi.org/10.1007/s11746-999-0102-7.

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14

Hamon, DPG, JW Holman, and RA Massywestropp. "The Synthesis of an Arylperhydronaphthalenol, an Efficient Chiral Auxiliary." Australian Journal of Chemistry 46, no. 5 (1993): 593. http://dx.doi.org/10.1071/ch9930593.

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15

Cambie, C., William A. Denny, Michael P. Hay, Lorna H. Mitchell, Peter S. Rutledge, and Paul D. Woodgate. "Modifications of Rings B and C of Podocarpic Acid: Towards the Synthesis of Quassinoids Richard." Australian Journal of Chemistry 52, no. 1 (1999): 7. http://dx.doi.org/10.1071/c98015.

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Attempts to alkylate products from Birch reductions of derivatives of podocarpic acid are reported. Attempted reductive silylation of ring C of methyl 12-methoxypodocarpa-8,11,13-trien-19-oate (5) gives products of C4 ester reduction only. The enantiopure form of the bis(ethylene acetal) (15) of 19-norpodocarp-8-ene-3,12-dione, a potentially useful intermediate for quassinoid synthesis, has been prepared from the ketone (34). Functionality at C8 on the β-face has been successfully introduced by abnormal Reimer–Tiemann reactions of podocarpic acid (2) and its 13-methyl derivative (10). The satu

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16

CAMBIE, R. C., P. K. DAVY, L. H. MITCHELL, C. E. F. RICKARD, and P. S. RUTLEDGE. "ChemInform Abstract: Oxidative Decarboxylation of Podocarpic Acid Derivatives." ChemInform 29, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199849232.

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17

CAMBIE, R. C., P. I. HIGGS, P. S. RUTLEDGE, and P. D. WOODGATE. "ChemInform Abstract: Aryne Chemistry of Podocarpic Acid Derivatives." ChemInform 25, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199452212.

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18

BENDALL, J. G., R. C. CAMBIE, A. C. GRIMSDALE, P. S. RUTLEDGE, and P. D. WOODGATE. "ChemInform Abstract: Synthesis of Winterin from Podocarpic Acid." ChemInform 23, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199237317.

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19

CAMBIE, R. C., M. R. METZLER, P. S. RUTLEDGE, and P. D. WOODGATE. "ChemInform Abstract: Organoiron Complexes of Podocarpic Acid Derivatives." ChemInform 22, no. 8 (2010): no. http://dx.doi.org/10.1002/chin.199108279.

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20

CAMBIE, R. C., P. S. RUTLEDGE, and P. D. WOODGATE. "ChemInform Abstract: Invited Review. Transformations of Podocarpic Acid." ChemInform 25, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199403287.

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21

CAMBIE, R. C., M. R. METZLER, C. E. F. RICKARD, P. S. RUTLEDGE, and P. D. WOODGATE. "ChemInform Abstract: Organomanganese Complexes of Podocarpic Acid Derivatives." ChemInform 23, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199223242.

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22

Cambie, RC, GR Clark, ME Goeth та ін. "Chemistry of the Podocarpaceae. LXXIV. The Conversion of Podocarpic Acid Into γ-Bicyclohomofarnesals". Australian Journal of Chemistry 42, № 4 (1989): 497. http://dx.doi.org/10.1071/ch9890497.

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Podocarpic acid (15) has been converted into the ambergris odorant γ-bicyclohomofarnesal (1) and two analogues (2) and (3). The stereochemistry of the intermediate keto ester (24) has been confirmed by a single-crystal X-ray determination.

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23

Cambie, RC, PI Higgs, PS Rutledge, and PD Woodgate. "Annulations of Podocarpic Acid Derivatives via an Aryne Intermediate." Australian Journal of Chemistry 47, no. 10 (1994): 1815. http://dx.doi.org/10.1071/ch9941815.

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The cycloaddition of substituted furans to the diterpenoid aryne (39), generated by in situ diazotization of the anthranilic acid (1) followed by cleavage of the annulated 1,4- epoxydecahydrochrysenes, provides a convenient method for the preparation in high yield of the previously unknown 1-substituted octahydrochrysen-4-ols. Use of 1,3-dipoles under the same procedure, or under a modified procedure involving pre-isolation of the diazonium tetrafluoroborate salt (9), gave novel annulated heterocyclic products directly. Attempted [2+2] cycloadditions of electron-rich alkenes to the diterpenoid

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24

Banerjee, Asish K., Dhanonjoy Nasipuri, and Satyesh C. Pakrashi. "A simple and highly stereoselective route to (.+-.)-podocarpic acid." Journal of Organic Chemistry 55, no. 12 (1990): 3952–54. http://dx.doi.org/10.1021/jo00299a047.

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25

Miles, D. Howard, Dong Seok Lho, Vallapa Chittawong, and Allen Matthew Payne. "Reactions of podocarpic acid derivatives with thallium(III) nitrate." Journal of Organic Chemistry 55, no. 13 (1990): 4034–36. http://dx.doi.org/10.1021/jo00300a016.

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26

CAMBIE, R. C., M. R. METZLER, P. S. RUTLEDGE, and P. D. WOODGATE. "ChemInform Abstract: Synthesis of Benzannulated Derivatives of Podocarpic Acid." ChemInform 23, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199203233.

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27

CAMBIE, R. C., C. E. F. RICKARD, and G. A. STRANGE. "ChemInform Abstract: Utilization of Podocarpic Acid for Nagilactone Synthesis." ChemInform 29, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199806217.

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28

Bendall, JG, RC Cambie, PS Rutledge, RJ Stevenson, and PD Woodgate. "Copper(I)-Mediated Oxygenation of Diterpenoids; Three Routes to Catechol Derivatives." Australian Journal of Chemistry 47, no. 3 (1994): 487. http://dx.doi.org/10.1071/ch9940487.

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Derivatives of totarol (1) and podocarpic acid (8) have been oxygenated in ring C via their corresponding carbamates, or aryl bromides, to form catechol derivatives. These oxygenations have been accomplished by the use of copper(I), both in stoichiometric and in catalytic quantities.

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29

He, Wei, Ashvin Gavai, Fu-Chih Huang, et al. "Novel cytokine release inhibitors. Part IV: Analogs of podocarpic acid." Bioorganic & Medicinal Chemistry Letters 9, no. 3 (1999): 469–74. http://dx.doi.org/10.1016/s0960-894x(99)00023-2.

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30

Cambie, RC, PS Rutledge, RJ Stevenson, and PD Woodgate. "Synthesis of Phthalide Derivatives of Podocarpic Acid Via Directed ortho Metalation: a Route to Highly Substituted Octahydrochrysene Derivatives." Australian Journal of Chemistry 47, no. 5 (1994): 913. http://dx.doi.org/10.1071/ch9940913.

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Two phthalide derivatives (7) and (8) have been prepared from podocarpic acid (1) via directed ortho metallation. The ring-c aromatic 16-oxa-17-oxo androstane analogue (8) was reacted with dimethyl acetylenedicarboxylate to give the 1,4-epoxy decahydrochrysene derivatives (9) and (10). The stereoisomer (10) was aromatized under acidic conditions to give the chrysen-1-ol derivative (11).

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31

Burnell, Robert H., and Jean-Marc Dufour. "The conversion of podocarpic acid to hexahydrophenalene derivatives: an approach to the synthesis of edulone A." Canadian Journal of Chemistry 65, no. 1 (1987): 21–25. http://dx.doi.org/10.1139/v87-005.

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To test the feasibility of a biogenetically inspired synthesis of edulone A 1, podocarpic acid 3a has been transformed into a substituted hexahydrophenalene 16b. The critical steps involve introduction of a double bond into the A ring, cleavage by ozone, and, after suitable manipulation, an epoxy-arene cyclization. A second product from this cyclization is an octahydrophenaleno[1,9-bc]furan 17.

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32

Cambie, Richard C., Lorna H. Mitchell, and Peter S. Rutledge. "A Synthesis of Triptoquinones D, E, and F from Podocarpic Acid." Australian Journal of Chemistry 51, no. 10 (1998): 931. http://dx.doi.org/10.1071/c98020.

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The First total synthesis of enantiopure triptoquinone F (6) starting from podocarpic acid (10) is reported, as well as formal syntheses of enantiopure triptoquinones D (4) and E (5). An acid-promoted Fries rearrangement of a benzannulated lactone (14) has been used as a direct, moderately high yielding route for introduction of C11 functionality. Treatment of methyl 12-methoxypodocarpa-8,11,13-trien-19-oate (11) with t-butylhydroperoxide and a catalytic amount of ruthenium(III) chloride gives a mixture (1 : 1) of diastereomeric t-butylcyclohexadienones (26) and (28).

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33

Bendall, JG, RC Cambie, PS Rutledge, and PD Woodgate. "Investigation of the Structures of Some Natural Products From the Neem Tree." Australian Journal of Chemistry 46, no. 12 (1993): 1825. http://dx.doi.org/10.1071/ch9931825.

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Podocarpic acid (1) and totarol (2) have been converted into five diterpenoids reported to have been isolated from the Neem tree. The synthetic diterpenoids have been compared with the naturally occurring diterpenoids but only the structure of nimbidiol (23) has been confirmed. The structure for margosolone, which was reported as (19), has been revised to (20) after synthesis of both (19) and (20).

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34

Cambie, Richard C., Maria do Céu Costa, Paul D. Woodgate, et al. "Oxidations of 12-Deoxy-, 12-Hydroxy-, 12-Methoxy-, and 12-Hydroxy-13-methoxy-podocarpa-8,11,13-triene Derivatives." Australian Journal of Chemistry 51, no. 1 (1998): 37. http://dx.doi.org/10.1071/c97046.

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Methods for the oxidation of the aryl ring of derivatives of podocarpic acid have been examined. Oxidation of methyl 12-hydroxypodocarpa-8,11,13-trien-19-oate (2) with phenyliodonium diacetate in various solvents gives 8β-substituted dienones. An 8β-chloro dienone is formed during oxidation of the phenol (2) with t-butyl hypochlorite. Oxidation of (2) with dimethyldioxiran gives mainly the 7-ketone (13) but also affords the novel ε-lactone (26), while treatment with ruthenium tetraoxide also affords products of benzylic oxidation. Oxidation of methyl podocarpa-8,11,13-trien-19-oate (4) with m-

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35

Snider, Barry B., Raju Mohan, and Steven A. Kates. "Manganese(III)-based oxidative free-radical cyclization. Synthesis of (.+-.)-podocarpic acid." Journal of Organic Chemistry 50, no. 19 (1985): 3659–61. http://dx.doi.org/10.1021/jo00219a054.

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36

CAMBIE, R. C., P. I. HIGGS, P. S. RUTLEDGE, and P. D. WOODGATE. "ChemInform Abstract: Annulations of Podocarpic Acid Derivatives via an Aryne Intermediate." ChemInform 26, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199507201.

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37

Burnell, Robert H., André Andersen, Martine Néron, and Sylvain Savard. "Synthesis of coleon C tri-O-methyl ether." Canadian Journal of Chemistry 63, no. 10 (1985): 2769–76. http://dx.doi.org/10.1139/v85-461.

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Starting from podocarpic acid, two model preparations are described leading to p-quinones suitably functionalized as intermediates in the synthesis of coleon C. The proper p-quinone was obtained by a regio- and stereo-selective route and, following steps previously found effective for the preparation of coleon U, a synthesis of tri-O-methyl coleon C has been achieved. Some of the by-products encountered have also been identified.

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38

Banerjee, Ajoy K., Julio C. Acevedo, and Nieves Canudas-González. "The Utility of Podocarpic Acid in the Synthesis of Naturally Occurring Terpenes." Bulletin des Sociétés Chimiques Belges 99, no. 1 (2010): 9–28. http://dx.doi.org/10.1002/bscb.19900990103.

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39

He, Wei, and et al et al. "ChemInform Abstract: Novel Cytokine Release Inhibitors. Part 4. Analogues of Podocarpic Acid." ChemInform 30, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199925164.

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40

Baraka, Hany. "Microbial Transformation of Podocarpic Acid and Evaluation of Transformation Products for Antioxidant Activity." Planta Medica 76, no. 08 (2010): 815–17. http://dx.doi.org/10.1055/s-0029-1240738.

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41

Woo, Kyoungja, Yang Cao, Huazhi Li, et al. "Single and double nucleophilic addition to methylated podocarpic acid coordinated to manganese tricarbonyl." Journal of Organometallic Chemistry 630, no. 1 (2001): 84–87. http://dx.doi.org/10.1016/s0022-328x(01)00888-9.

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42

CAMBIE, R. C., L. H. MITCHELL, and P. S. RUTLEDGE. "ChemInform Abstract: A Synthesis of Triptoquinones D, E, and F from Podocarpic Acid." ChemInform 30, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199907193.

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43

CAMBIE, R. C., M. P. HAY, L. LARSEN, C. E. F. RICKARD, P. S. RUTLEDGE, and P. D. WOODGATE. "ChemInform Abstract: Ring A Modifications of Podocarpic Acid: Towards the Synthesis of Quassinoids." ChemInform 22, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199136249.

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44

La Bella, Angela, Francesca Leonelli, Luisa Migneco, and Rinaldo Marini Bettolo. "(+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids †." Molecules 21, no. 9 (2016): 1197. http://dx.doi.org/10.3390/molecules21091197.

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45

Cambie, RC, PI Higgs, KC Lee, et al. "Directed ortho Metalation Studies on Podocarpic Acid Derivatives: Advantageous Use of a LICKOR Base." Australian Journal of Chemistry 44, no. 10 (1991): 1465. http://dx.doi.org/10.1071/ch9911465.

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Methyl 13-(N,N- diethylcarbamoyl )-12-methoxypodocarpa-8,11,13-trien-19-oate (2), 13-(N,N- diethylcarbamoyl )-12,19-dimethoxypodocarpa-8,11,13-triene (8) and N,N-diethyl-2-methoxy-4,5-dimethylbenzamide (15) were prepared for studies involving lithiation directed ortho to the tertiary amide group, in which the use of a LICKOR base was advantageous. Some dynamic features of the n.m.r. spectra of the amides are discussed. Oxazoline derivatives of both tile monocyclic and diterpenoid compounds were synthesized.

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46

Cambie, Richard C., John H. M. Hill, Peter S. Rutledge, Ralph J. Stevenson, and Paul D. Woodgate. "Benzannulation of podocarpic acid derivatives via directed ortho metallation and lithium-copper(I) transmetallation." Journal of Organometallic Chemistry 474, no. 1-2 (1994): 31–41. http://dx.doi.org/10.1016/0022-328x(94)84042-3.

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47

Cambie, Richard C., Peter S. Rutledge, Ralph J. Stevenson та Paul D. Woodgate. "Cyclopentaannulation of podocarpic acid derivatives via (η6-arene)tricarbonylchromium(O) complexes; ring D modification". Journal of Organometallic Chemistry 471, № 1-2 (1994): 133–47. http://dx.doi.org/10.1016/0022-328x(94)88117-0.

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48

Shahinozzaman, Md, Moutushi Islam, Bristy Basak, et al. "A review on chemistry, source and therapeutic potential of lambertianic acid." Zeitschrift für Naturforschung C 76, no. 9-10 (2021): 347–56. http://dx.doi.org/10.1515/znc-2020-0267.

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Abstract Lambertianic acid (LA) is a diterpene bioactive compound mainly purified from different species of Pinus. It is an optical isomer of another natural compound daniellic acid and was firstly purified from Pinus lambertiana. LA can be synthesized in laboratory from podocarpic acid. It has been reported to have potential health benefits in attenuating obesity, allergies and different cancers including breast, liver, lung and prostate cancer. It exhibits anticancer properties through inhibiting cancer cell proliferation and survival, and inducing apoptosis, targeting major signalling compo

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49

Cochrane, E. Jane, S. Warren Lazer, John T. Pinhey, and John D. Whitby. "Stereoid cd-ring synthons from podocarpic acid by use of the barton radical decarboxylation reaction." Tetrahedron Letters 30, no. 50 (1989): 7111–14. http://dx.doi.org/10.1016/s0040-4039(01)93437-9.

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50

Cambie, Richard C., Michael R. Metzler, Clifton E. F. Rickard, Peter S. Rutledge та Paul D. Woodgate. "Reactions of η2-tetracarbonylmanganese complexes derived from podocarpic acid with electrophiles; functionalization of ring C". Journal of Organometallic Chemistry 431, № 2 (1992): 177–98. http://dx.doi.org/10.1016/0022-328x(92)80117-g.

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