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Journal articles on the topic 'Tetracyclic diterpenes'

Author: Grafiati

Published: 22 February 2023

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1

Shen, Yong, Wen-Juan Liang, Ya-Na Shi, Edward J. Kennelly, and Da-Ke Zhao. "Structural diversity, bioactivities, and biosynthesis of natural diterpenoid alkaloids." Natural Product Reports 37, no. 6 (2020): 763–96. http://dx.doi.org/10.1039/d0np00002g.

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2

Chen, Yan-Ni, Xiao Ding, Dong-Mei Li, Mao Sun, Lei Yang, Yu Zhang, Ying-Tong Di, Xin Fang, and Xiao-Jiang Hao. "Diterpenoids with an unprecedented ring system from Euphorbia peplus and their activities in the lysosomal-autophagy pathway." Organic & Biomolecular Chemistry 19, no. 7 (2021): 1541–45. http://dx.doi.org/10.1039/d0ob02414g.

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3

Marcos, Isidro S., Rosalina F. Moro, Santiago Carballares M., and Julio G. Urones. "Cyclization of Bicyclic Diterpenes Promoted by SmI2. Synthesis of Tri- and Tetracyclic Diterpenes." Synlett 2002, no. 03 (2002): 0458–62. http://dx.doi.org/10.1055/s-2002-20465.

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4

Vasas, Andrea, Judit Hohmann, Peter Forgo, and Pál Szabó. "New tri- and tetracyclic diterpenes from Euphorbia villosa." Tetrahedron 60, no. 23 (May 2004): 5025–30. http://dx.doi.org/10.1016/j.tet.2004.04.028.

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5

Marcos, I. S., M. A. Cubillo, R. F. Moro, S. Carballares, D. Díez, P. Basabe, C. F. Llamazares, et al. "Synthesis of tri- and tetracyclic diterpenes. Cyclisations promoted by SmI2." Tetrahedron 61, no. 4 (January 2005): 977–1003. http://dx.doi.org/10.1016/j.tet.2004.09.116.

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6

GOLDSMITH, D. "ChemInform Abstract: The Total Synthesis of Tri- and Tetracyclic Diterpenes." ChemInform 23, no. 47 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199247301.

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7

Chen, De-Lin, Feng-Peng Wang, and Xiao-Yu Liu. "A convergent approach to the tetracyclic core of atisane diterpenes." Chinese Chemical Letters 27, no. 1 (January 2016): 59–62. http://dx.doi.org/10.1016/j.cclet.2015.09.005.

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8

Adelin, Emilie, Claudine Servy, Marie-Thérèse Martin, Guillaume Arcile, Bogdan I. Iorga, Pascal Retailleau, Mercedes Bonfill, and Jamal Ouazzani. "Bicyclic and tetracyclic diterpenes from a Trichoderma symbiont of Taxus baccata." Phytochemistry 97 (January 2014): 55–61. http://dx.doi.org/10.1016/j.phytochem.2013.10.016.

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9

Smyrniotopoulos, Vangelis, Constantinos Vagias, Mukhlesur M Rahman, Simon Gibbons, and Vassilios Roussis. "Ioniols I and II, Tetracyclic Diterpenes with Antibacterial Activity, fromSphaerococcus coronopifolius." Chemistry & Biodiversity 7, no. 3 (March 2010): 666–76. http://dx.doi.org/10.1002/cbdv.200900026.

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10

Hayashi, Toshimitsu, Tomohiko Asai, and Ushio Sankawa. "Mevalonate-independent biosynthesis of bicyclic and tetracyclic diterpenes of Scoparia dulcis L." Tetrahedron Letters 40, no. 47 (November 1999): 8239–43. http://dx.doi.org/10.1016/s0040-4039(99)01748-7.

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11

García-Granados, Andrés, Antonio Martínez, M. Esther Onorato, and Jose M. Arias. "Microbial Transformation of Tetracyclic Diterpenes: Conversion of Ent-Kaurenones by Aspergillus niger." Journal of Natural Products 49, no. 1 (January 1986): 126–32. http://dx.doi.org/10.1021/np50043a016.

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12

Hou, Si-Hua, Yong-Qiang Tu, Shuang-Hu Wang, Chao-Chao Xi, Fu-Min Zhang, Shao-Hua Wang, Yan-Tao Li, and Lin Liu. "Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and Conidiogenone B." Angewandte Chemie International Edition 55, no. 14 (March 3, 2016): 4456–60. http://dx.doi.org/10.1002/anie.201600529.

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13

Hou, Si-Hua, Yong-Qiang Tu, Shuang-Hu Wang, Chao-Chao Xi, Fu-Min Zhang, Shao-Hua Wang, Yan-Tao Li, and Lin Liu. "Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and Conidiogenone B." Angewandte Chemie 128, no. 14 (March 3, 2016): 4532–36. http://dx.doi.org/10.1002/ange.201600529.

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14

Rigby, James H., and Stephane V. Cuisiat. "Synthetic studies on the ingenane diterpenes. Construction of a tetracyclic 8-isoingenane model." Journal of Organic Chemistry 58, no. 23 (November 1993): 6286–91. http://dx.doi.org/10.1021/jo00075a023.

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15

Garciá-Granados, Andrés, Antonio Martinez, M. Esther Onorato, and Jose M. Arias. "Microbial Transformation of Tetracyclic Diterpenes: Conversion of Ent-Beyerenes by Rhizopus nigricans Cultures." Journal of Natural Products 48, no. 3 (May 1985): 371–75. http://dx.doi.org/10.1021/np50039a004.

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16

Bellino, Aurora, and Pietro Venturella. "Some Transformations of Episideridiol in the Synthesis of Naturally Occurring Tetracyclic Kaurene Diterpenes." Journal of Natural Products 51, no. 6 (November 1988): 1246–48. http://dx.doi.org/10.1021/np50060a033.

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17

Hou, Si-Hua, Yong-Qiang Tu, Shuang-Hu Wang, Chao-Chao Xi, Fu-Min Zhang, Shao-Hua Wang, Yan-Tao Li, and Lin Liu. "Frontispiz: Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and Conidiogenone B." Angewandte Chemie 128, no. 14 (March 21, 2016): n/a. http://dx.doi.org/10.1002/ange.201681461.

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18

Hou, Si-Hua, Yong-Qiang Tu, Shuang-Hu Wang, Chao-Chao Xi, Fu-Min Zhang, Shao-Hua Wang, Yan-Tao Li, and Lin Liu. "Frontispiece: Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and Conidiogenone B." Angewandte Chemie International Edition 55, no. 14 (March 21, 2016): n/a. http://dx.doi.org/10.1002/anie.201681461.

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19

Ola, Antonius R. B., Anna-Marie Babey, Cherie Motti, and Bruce F. Bowden. "Aplysiols C - E, Brominated Triterpene Polyethers from the Marine Alga Chondria armata and a Revision of the Structure of Aplysiol B." Australian Journal of Chemistry 63, no. 6 (2010): 907. http://dx.doi.org/10.1071/ch10081.

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Three new brominated triterpene polyethers, aplysiols C–E (1–3), were isolated from extracts of the red alga Chondria armata. Structures were determined by comparison with the closely related metabolite, aplysiol B, which was previously reported from the anaspidean mollusc Aplysia dactylomela. The relative stereochemistry of the tetracyclic ring system was determined from 1D gradient selective NOESY experiments and from biogenetic considerations that support a revision of the stereochemistry proposed for aplysiol B. In addition, three known brominated C15 acetogenin acetylenic ethers: (–)-pinnatifidenyne, (+)-laurenyne, and (+)-obtusenyne, two brominated diterpenes: (–)-ent-angasiol and (–)-ent-angasiol acetate, and the symmetrical halogenated triterpene polyether intricatetraol were isolated.

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20

Garcia-Granados, Andres, Antonio Martinez, Antonio Ortiz, Maria Esther Onorato, and Jose Maria Arias. "Microbial Transformation of Tetracyclic Diterpenes: Conversion of ent-Kaurenones by Curvularia and Rhizopus Strains." Journal of Natural Products 53, no. 2 (March 1990): 441–50. http://dx.doi.org/10.1021/np50068a024.

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21

Smyrniotopoulos, Vangelis, Constantinos Vagias, Mukhlesur M. Rahman, Simon Gibbons, and Vassilios Roussis. "ChemInform Abstract: Ioniols I and II, Tetracyclic Diterpenes with Antibacterial Activity, from Sphaerococcus coronopifolius." ChemInform 41, no. 28 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.201028187.

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22

Forster, Louise C., Jack K. Clegg, Karen L. Cheney, and Mary J. Garson. "Expanding the Repertoire of Spongian-16-One Derivatives in Australian Nudibranchs of the Genus Goniobranchus and Evaluation of Their Anatomical Distribution." Marine Drugs 19, no. 12 (November 29, 2021): 680. http://dx.doi.org/10.3390/md19120680.

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Extracts of the mantle and viscera of the Indo-Pacific nudibranchs Goniobranchus aureopurpureus and Goniobranchus sp. 1 afforded 11 new diterpenoids (1–11), all of which possess a tetracyclic spongian-16-one scaffold with extensive oxidation at C-6, C-7, C-11, C-12, C-13, and/or C-20. The structures and relative configuration were investigated by NMR experiments, while X-ray crystallography provided the absolute configuration of 1, including a 2′S configuration for the 2-methylbutanoate substituent located at C-7. Dissection of animal tissue revealed that the mantle and viscera tissues differed in their metabolite composition with diterpenes 1–11 present in the mantle tissue of the two nudibranch species.

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23

Moiseenkov, A. M., V. V. Veselovskii, V. A. Dragan, A. V. Ignatenko, and Yu A. Strelenko. "Electrophilic cyclization of ?-monoterpenols as a model for the biosynthesis of tri- and tetracyclic diterpenes." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 39, no. 6 (June 1990): 1233–37. http://dx.doi.org/10.1007/bf00962389.

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24

Castrillo, Antonio, Beatriz de las Heras, Sonsoles Hortelano, Benjamı́n Rodrı́guez, Angel Villar, and Lisardo Boscá. "Inhibition of the Nuclear Factor κB (NF-κB) Pathway by Tetracyclic Kaurene Diterpenes in Macrophages." Journal of Biological Chemistry 276, no. 19 (February 9, 2001): 15854–60. http://dx.doi.org/10.1074/jbc.m100010200.

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25

RIGBY, J. H., and S. V. CUISIAT. "ChemInform Abstract: Synthetic Studies on the Ingenane Diterpenes. Construction of a Tetracyclic 8-Isoingenane Model." ChemInform 25, no. 8 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199408271.

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26

Wang, Xiaohong, Rui Jiang, Zizhen Liu, Weirui Liu, Meng Xie, Shengli Wei, and Gaimei She. "Phytochemicals and Biological Activities of Poisonous Genera of Ericaceae in China." Natural Product Communications 9, no. 3 (March 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900333.

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The family Ericaceae is comprised of about 70 genera of which about 20 are found throughout China. Of these Ledum, Rhododendron, Enkianthus, Pieris, Craibiodendron, Gaultheria, Vaccinium, and Leucothoe are regarded as poisonous. Many species of these poisonous genera are used as Chinese herbal medicines for the treatment of, for example, inflammation, asthma, and coughs. Modern research has demonstrated that the toxic ingredients of these poisonous genera are chiefly tetracyclic diterpenes, which have adverse effects on the digestive, cardiovascular and nervous systems. Because various species of these poisonous genera also have medicinal functions, extensive studies of these plants have led to the identification of many kinds of compound. This paper compiles 306 compounds from the eight poisonous genera, reported in 141 references.

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27

Herrera-Acevedo, Chonny, Areli Flores-Gaspar, Luciana Scotti, Francisco Jaime Bezerra Mendonça-Junior, Marcus Tullius Scotti, and Ericsson Coy-Barrera. "Identification of Kaurane-Type Diterpenes as Inhibitors of Leishmania Pteridine Reductase I." Molecules 26, no. 11 (May 21, 2021): 3076. http://dx.doi.org/10.3390/molecules26113076.

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The current treatments against Leishmania parasites present high toxicity and multiple side effects, which makes the control and elimination of leishmaniasis challenging. Natural products constitute an interesting and diverse chemical space for the identification of new antileishmanial drugs. To identify new drug options, an in-house database of 360 kauranes (tetracyclic diterpenes) was generated, and a combined ligand- and structure-based virtual screening (VS) approach was performed to select potential inhibitors of Leishmania major (Lm) pteridine reductase I (PTR1). The best-ranked kauranes were employed to verify the validity of the VS approach through LmPTR1 enzyme inhibition assay. The half-maximal inhibitory concentration (IC50) values of selected bioactive compounds were examined using the random forest (RF) model (i.e., 2β-hydroxy-menth-6-en-5β-yl ent-kaurenoate (135) and 3α-cinnamoyloxy-ent-kaur-16-en-19-oic acid (302)) were below 10 μM. A compound similar to 302, 3α-p-coumaroyloxy-ent-kaur-16-en-19-oic acid (302a), was also synthesized and showed the highest activity against LmPTR1. Finally, molecular docking calculations and molecular dynamics simulations were performed for the VS-selected, most-active kauranes within the active sites of PTR1 hybrid models, generated from three Leishmania species that are known to cause cutaneous leishmaniasis in the new world (i.e., L. braziliensis, L. panamensis, and L. amazonensis) to explore the targeting potential of these kauranes to other species-dependent variants of this enzyme.

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28

O'Connor, Stephen J., Larry E. Overman, and Paul V. Rucker. "Use of Sequential Intramolecular Heck Cyclizations for Preparing Bicyclo[3.2.1]octane Fragments of Tetracyclic Stemodane and Stemarane Diterpenes." Synlett 2001, Special Issue (2001): 1009–12. http://dx.doi.org/10.1055/s-2001-14648.

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29

Thawabteh, Amin Mahmood, Alà Thawabteh, Filomena Lelario, Sabino Aurelio Bufo, and Laura Scrano. "Classification, Toxicity and Bioactivity of Natural Diterpenoid Alkaloids." Molecules 26, no. 13 (July 5, 2021): 4103. http://dx.doi.org/10.3390/molecules26134103.

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Diterpenoid alkaloids are natural compounds having complex structural features with many stereo-centres originating from the amination of natural tetracyclic diterpenes and produced primarily from plants in the Aconitum, Delphinium, Consolida genera. Corals, Xenia, Okinawan/Clavularia, Alcyonacea (soft corals) and marine sponges are rich sources of diterpenoids, despite the difficulty to access them and the lack of availability. Researchers have long been concerned with the potential beneficial or harmful effects of diterpenoid alkaloids due to their structural complexity, which accounts for their use as pharmaceuticals as well as their lousy reputation as toxic substances. Compounds belonging to this unique and fascinating family of natural products exhibit a broad spectrum of biological activities. Some of these compounds are on the list of clinical drugs, while others act as incredibly potent neurotoxins. Despite numerous attempts to prepare synthetic products, this review only introduces the natural diterpenoid alkaloids, describing ‘compounds’ structures and classifications and their toxicity and bioactivity. The purpose of the review is to highlight some existing relationships between the presence of substituents in the structure of such molecules and their recognised bioactivity.

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30

Hoscheid, Jaqueline, and Mara Lane Carvalho Cardoso. "Sucupira as a Potential Plant for Arthritis Treatment and Other Diseases." Arthritis 2015 (November 3, 2015): 1–12. http://dx.doi.org/10.1155/2015/379459.

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Trees of the genus Pterodon, commonly known as “sucupira-branca” or “faveira,” are native to central Brazil. The Pterodon fruits are traditionally used in ethnomedicine as an infusion, in small doses, and at regular time intervals as an antirheumatic, anti-inflammatory, tonic, and depurative agent. The various compounds present in the Pterodon class are, generally, water-insoluble and derived from the fusion of high-molecular weight pentacarbonate units. Scientific research has shown that the major compounds isolated from Pterodon species are linear and/or tetracyclic diterpenes with vouacapane skeletons that partly underlie the pharmacological activities of the fruit-derived oil. Material from Pterodon species has several biological properties, such as analgesic, anti-inflammatory, and anticancer effects. Therefore, recent studies have sought to microencapsulate these extracts to protect them from potential chemical degradation and improve their water solubility, ensuring greater stability and quality of the end products. This review presents a succinct overview of the available scientific evidence of the biological activity and toxicity of Pterodon species in addition to other important aspects, including phytochemical and technological features.

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31

Braish, T. F., J. C. Saddler, and P. L. Fuchs. "Syntheses via vinyl sulfones. 28. Seven-ring annulation. A linch-pin approach to a tetracyclic precursor of the lathrane diterpenes." Journal of Organic Chemistry 53, no. 16 (August 1988): 3647–58. http://dx.doi.org/10.1021/jo00251a001.

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32

O'Connor, Stephen J., Larry E. Overman, and Paul V. Rucker. "ChemInform Abstract: Use of Sequential Intramolecular Heck Cyclizations for Preparing Bicyclo[3.2.1]octane Fragments of Tetracyclic Stemodane and Stemarane Diterpenes." ChemInform 32, no. 42 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200142213.

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33

Pomilio, Alicia B., Elvira M. Falzoni, and Arturo A. Vitale. "Toxic Chemical Compounds of the Solanaceae." Natural Product Communications 3, no. 4 (April 2008): 1934578X0800300. http://dx.doi.org/10.1177/1934578x0800300420.

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The Solanaceae is comprised of some 2500 species of cosmopolitan plants, especially native to the American continent. They have great value as food, like the well-known potato, tomato and eggplants, and medicines, like species of Atropa, Withania and Physalis, but many plants of this family are toxic, and sometimes lethal to mammals, in particular to man. Some of them also produce hallucinations and perceptual changes. The toxic species of this family are characterized by the occurrence of a variety of chemical compounds, some of which are responsible for the toxicity and lethality observed after ingestion, while others are suspected to be toxic. In this review, the following toxic compounds belonging to different members of the Solanaceae family are described: Tropane alkaloids ( Atropa, Datura, Hyoscyamus, Mandragora); pyrrolidine and pyrrolic alkaloids ( Nierembergia, Physalis, Solanum); protoalkaloids ( Nierembergia); glycoalkaloids ( Lycopersicon, Solanum); nicotine ( Nicotiana); cardenolides ( Cestrum, Nierembergia); capsaicinoids ( Capsicum); kaurene-type tetracyclic diterpenes ( Cestrum); steroidal glycosides ( Cestrum, Solanum); 1,25-dihydroxyvitamin D3 and vitamin D3 ( Cestrum, Solanum, Nierembergia); and withasteroids, withanolides ( Withania), and physalins ( Physalis). Other bioactive chemical constituents of members of this family are sugar esters and lectins. Phenylpropanoids are not included in this paper.

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34

Aubert, Corinne, Jean Pierre Gotteland, and Max Malacria. "Stereoselective access to the basic skeleton of tetracyclic diterpenes via a sequence of consecutive [3 + 2], [2 + 2 + 2], and [4 + 2] cycloaddition reactions." Journal of Organic Chemistry 58, no. 16 (July 1993): 4298–305. http://dx.doi.org/10.1021/jo00068a026.

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35

Gotteland, Jean-Pierre, and Max Malacria. "Stereoselective Access to the Basic Skeleton of Tetracyclic Diterpenes via a Sequence of Consecutive [3+2], [2+2+2], and [4+2] Cycloaddition Reactions. Studies on the Stereoselectivity of the Intramolecular Diels-Alder Reaction." Synlett 1990, no. 11 (1990): 667–69. http://dx.doi.org/10.1055/s-1990-21203.

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36

Yi-Li, Ding, and Jia Zhong-Jian. "Tetracyclic diterpenols from Euphorbia sieboldiana." Phytochemistry 30, no. 7 (January 1991): 2413–15. http://dx.doi.org/10.1016/0031-9422(91)83666-9.

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37

Xu, Jun-Ju, Jun-Ting Fan, Guang-Zhi Zeng, and Ning-Hua Tan. "A New Tetracyclic Diterpene from Jatropha curcas." Helvetica Chimica Acta 94, no. 5 (May 2011): 842–46. http://dx.doi.org/10.1002/hlca.201000313.

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38

Ferreira, Maria-José U., Ana Margarida Madureira, and José R. Ascenso. "A Tetracyclic diterpene and triterpenes from euphorbia segetalis." Phytochemistry 49, no. 1 (September 1998): 179–83. http://dx.doi.org/10.1016/s0031-9422(97)01011-x.

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39

Ferreira, Maria-José U., and José R. Ascenso. "Steroids and a tetracyclic diterpene from Euphorbia boetica." Phytochemistry 51, no. 3 (June 1999): 439–44. http://dx.doi.org/10.1016/s0031-9422(98)00739-0.

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40

von Schwartzenberg, K., W. Schultze, and H. Kassner. "The moss Physcomitrella patens releases a tetracyclic diterpene." Plant Cell Reports 22, no. 10 (February 12, 2004): 780–86. http://dx.doi.org/10.1007/s00299-004-0754-6.

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41

Perera, Wilmer H., and James D. McChesney. "Approaches toward the Separation, Modification, Identification and Scale up Purification of Tetracyclic Diterpene Glycosides from Stevia rebaudiana (Bertoni) Bertoni." Molecules 26, no. 7 (March 29, 2021): 1915. http://dx.doi.org/10.3390/molecules26071915.

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Stevia rebaudiana (Bertoni) Bertoni is a plant species native to Brazil and Paraguay well-known by the sweet taste of their leaves. Since the recognition of rebaudioside A and other steviol glycosides as generally recognized as safe by the United States Food and Drug Administration in 2008 and grant of marketing approval by the European Union in 2011, the species has been widely cultivated and studied in several countries. Several efforts have been dedicated to the isolation and structure elucidation of minor components searching for novel non-caloric sugar substitutes with improved organoleptic properties. The present review provides an overview of the main chemical approaches found in the literature for identification and structural differentiation of diterpene glycosides from Stevia rebaudiana: High-performance Thin-Layer Chromatography, High-Performance Liquid Chromatography, Electrospray Ionization Mass Spectrometry and Nuclear Magnetic Resonance Spectroscopy. Modification of diterpene glycosides by chemical and enzymatic reactions together with some strategies to scale up of the purification process saving costs are also discussed. A list of natural diterpene glycosides, some examples of chemically modified and of enzymatically modified diterpene glycosides reported from 1931 to February 2021 were compiled using the scientific databases Google Scholar, ScienceDirect and PubMed.

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42

Lee, Jung-Bum, Tomoya Ohmura, and Yoshimi Yamamura. "Functional Characterization of Three Diterpene Synthases Responsible for Tetracyclic Diterpene Biosynthesis in Scoparia dulcis." Plants 12, no. 1 (December 23, 2022): 69. http://dx.doi.org/10.3390/plants12010069.

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Scoparia dulcis produces unique biologically active diterpenoids such as scopadulcic acid B (SDB). They are biosynthesized from geranylgeranyl diphosphate (GGPP) via syn-copalyl diphosphate (syn-CPP) and scopadulanol as an important key intermediate. In this paper, we functionally characterized three diterpene synthases, SdCPS2, SdKSL1 and SdKSL2, from S. dulcis. The SdCPS2 catalyzed a cyclization reaction from GGPP to syn-CPP, and SdKSL1 did from syn-CPP to scopadulan-13α-ol. On the other hand, SdKSL2 was found to incorporate a non-sense mutation at 682. Therefore, we mutated the nucleotide residue from A to G in SdKSL2 to produce SdKSL2mut, and it was able to recover the catalytic function from syn-CPP to syn-aphidicol-16-ene, the precursor to scopadulin. From our results, SdCPS2 and SdKSL1 might be important key players for SDB biosynthesis in S. dulcis.

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43

Tanaka, Junichi, Irvina Nurrachmi, and Tatsuo Higa. "Umabanol, a New Tetracyclic Diterpene from a Marine Sponge." Chemistry Letters 26, no. 6 (June 1997): 489–90. http://dx.doi.org/10.1246/cl.1997.489.

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44

Petrov, Alexander A., Tonis Y. Pehk, Nadezhda S. Vorobieva, and Zinaida K. Zemskova. "Identification of some novel tetracyclic diterpene hydrocarbons in petroleum." Organic Geochemistry 12, no. 2 (January 1988): 151–56. http://dx.doi.org/10.1016/0146-6380(88)90251-3.

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45

Xu, Jun-Ju, Jun-Ting Fan, Guang-Zhi Zeng, and Ning-Hua Tan. "ChemInform Abstract: A New Tetracyclic Diterpene from Jatropha curcas." ChemInform 42, no. 36 (August 11, 2011): no. http://dx.doi.org/10.1002/chin.201136181.

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46

FERREIRA, M. J. U., A. M. MADUREIRA, and J. R. ASCENSO. "ChemInform Abstract: A Tetracyclic Diterpene and Triterpenes from Euphorbia segetalis." ChemInform 29, no. 52 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199852229.

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47

Chantrapromma, Suchada, Chotika Jeerapong, Worrapong Phupong, Ching Kheng Quah, and Hoong-Kun Fun. "Trichodermaerin: a diterpene lactone fromTrichoderma asperellum." Acta Crystallographica Section E Structure Reports Online 70, no. 4 (March 8, 2014): o408—o409. http://dx.doi.org/10.1107/s1600536814004632.

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Abstract:

The title compound, C20H28O3, known as `trichodermaerin' [systematic name: (4E)-4,9,15,16,16-pentamethyl-6-oxatetracyclo[10.3.1.01,10.05,9]hexadec-4-ene-7,13-dione], is a diterpene lactone which was isolated fromTrichoderma asperellum. The structure has a tetracycic 6–5–7–5 ring system, with the cyclohexanone ring adopting a twisted half-chair conformation and the cyclopentane ring adopting a half-chair conformation, whereas the cycloheptene and tetrahydrofurananone rings are in chair and envelope (with the methyl-substituted C atom as the flap) conformations, respectively. The three-dimensional architecture is stabilized by C—H...O interactions.

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48

Maertens, Gaëtan, Samuel Desjardins, and Sylvain Canesi. "Asymmetric synthesis of (+)-17-epi-methoxy-kauran-3-one through tandem oxidative polycyclization-pinacol process." Organic & Biomolecular Chemistry 14, no. 28 (2016): 6744–50. http://dx.doi.org/10.1039/c6ob01142j.

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Abstract:

A synthesis of (+)-17-epi-methoxy-kauran-3-one, an O-methylated isomer of the natural diterpene 17-hydroxy-kauran-3-one, has been achieved. The strategy is based on a diastereoselective oxidative polycyclization-pinacol tandem process consisting in transforming a functionalized phenol into a compact and complex tetracycle.

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49

Blasko, Gabor, Long Ze Lin, and Geoffrey A. Cordell. "Determination of a new tetracyclic diterpene skeleton through selective INEPT spectroscopy." Journal of Organic Chemistry 53, no. 26 (December 1988): 6113–15. http://dx.doi.org/10.1021/jo00261a026.

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50

TANAKA, J., I. NURRACHMI, and T. HIGA. "ChemInform Abstract: Umabanol, a New Tetracyclic Diterpene from a Marine Sponge." ChemInform 28, no. 45 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199745208.

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