Collect. Czech. Chem. Commun.
1969, 34, 582-592
https://doi.org/10.1135/cccc19690582
On terpenes. CXCVIII. Isolation and structure of pinguisone from Aneura pinguis (L.) DUM.
V. Benešová, Z. Samek, V. Herout and F. Šorm
Crossref Cited-by Linking
- Filipovic Sonja, Bijelic Ana, Bogdanovic Andrija, Radulovic Niko: Pinguisane-type sesquiterpenoids, unique secondary metabolites of liverworts: A review. Facta Univ Phys Chem Technol 2022, 20, 1. <https://doi.org/10.2298/FUPCT2201001F>
- Ge Shulin, Zhang Yongyan, Tan Zheng, Li Dawei, Dong Shunxi, Liu Xiaohua, Feng Xiaoming: Bimetallic Catalytic Tandem Reaction of Acyclic Enynones: Enantioselective Access to Tetrahydrobenzofuran Derivatives. Org. Lett. 2020, 22, 3551. <https://doi.org/10.1021/acs.orglett.0c00984>
- Sugiura Hirotaka, Yamazaki Shoko, Ogawa Akiya: Sequential Intramolecular Diels–Alder Reaction of 3‐Heteroaryl‐2‐propenylamides of Ethenetricarboxylate. Journal of Heterocyclic Chem 2019, 56, 2592. <https://doi.org/10.1002/jhet.3665>
- Wawrzyniak Rafał, Wasiak Wiesław, Jasiewicz Beata, Ludwiczuk Agnieszka, Bączkiewicz Alina, Buczkowska Katarzyna: High correlation of chemical composition with genotype in cryptic species of the liverwort Aneura pinguis. Phytochemistry 2018, 152, 134. <https://doi.org/10.1016/j.phytochem.2018.05.004>
- Yadav Jhillu Singh, Singh Shweta, Das Saibal: An Enantioselective Approach to Pinguisane Sesquiterpenes: Total Synthesis of (–)‐Pinguisenol and (–)‐Isonaviculol. Eur J Org Chem 2017, 2017, 2824. <https://doi.org/10.1002/ejoc.201700395>
- Liu Junjia, Marsini Maurice A., Bedell T. Aaron, Reider Paul J., Sorensen Erik J.: Diastereoselective syntheses of substituted cis-hydrindanones featuring sequential inter- and intramolecular Michael reactions. Tetrahedron 2016, 72, 3713. <https://doi.org/10.1016/j.tet.2016.03.039>
- Eagan James M., Hori Masahiro, Wu Jianbin, Kanyiva Kyalo Stephen, Snyder Scott A.: Synthesis and Applications of Hajos–Parrish Ketone Isomers. Angewandte Chemie 2015, 127, 7953. <https://doi.org/10.1002/ange.201500925>
- Eagan James M., Hori Masahiro, Wu Jianbin, Kanyiva Kyalo Stephen, Snyder Scott A.: Synthesis and Applications of Hajos–Parrish Ketone Isomers. Angew Chem Int Ed 2015, 54, 7842. <https://doi.org/10.1002/anie.201500925>
- Manna Susanta Kumar, Mandal Arabinda, Mondal Suresh Kumar, Samanta Shubhankar, Ray Jayanta K., Baidya Mahiuddin: Platinum(II)-Catalyzed Novel Synthesis of 3,4-Fused Furans. Synthetic Communications 2015, 45, 625. <https://doi.org/10.1080/00397911.2014.974615>
- Zhou Liejin, Zhang Mingrui, Li Wenbo, Zhang Junliang: Furan‐Based o‐Quinodimethanes by Gold‐Catalyzed Dehydrogenative Heterocyclization of 2‐(1‐Alkynyl)‐2‐alken‐1‐ones: A Modular Entry to 2,3‐Furan‐Fused Carbocycles. Angewandte Chemie 2014, 126, 6660. <https://doi.org/10.1002/ange.201403709>
- Zhou Liejin, Zhang Mingrui, Li Wenbo, Zhang Junliang: Furan‐Based o‐Quinodimethanes by Gold‐Catalyzed Dehydrogenative Heterocyclization of 2‐(1‐Alkynyl)‐2‐alken‐1‐ones: A Modular Entry to 2,3‐Furan‐Fused Carbocycles. Angew Chem Int Ed 2014, 53, 6542. <https://doi.org/10.1002/anie.201403709>
- Wawrzyniak Rafał, Wasiak Wiesław, Bączkiewicz Alina, Buczkowska Katarzyna: Volatile compounds in cryptic species of the Aneura pinguis complex and Aneura maxima (Marchantiophyta, Metzgeriidae). Phytochemistry 2014, 105, 115. <https://doi.org/10.1016/j.phytochem.2014.06.010>
- Sono Masakazu, Ise Natsuko, Shoji Tsutomu, Tori Motoo: Cyclizations Producing Hydrindanones with Two Methyl Groups at the Juncture Positions Mediated by Samarium Diiodide and Electrolysis. Molecules 2012, 17, 11079. <https://doi.org/10.3390/molecules170911079>
- Yang Young-Keun, Choi Jung-Hoon, Tae Jinsung: Synthesis of 2,3-Di- and 2,3,4-Trisubstituted Furans from 1,2-Dioxines Generated by an Enyne-RCM/Diels−Alder Reaction Sequence. J. Org. Chem. 2005, 70, 6995. <https://doi.org/10.1021/jo050957q>
- Méndez-Andino José, Paquette Leo A.: Convergent Regiodirected Assembly of 2,3-Disubstituted Furans. Org. Lett. 2000, 2, 4095. <https://doi.org/10.1021/ol000325k>
- TAZAKI Hiroyuki, IWASAKI Takeshi, KAWAKAMI Yukihiro, NABETA Kensuke: 1,2-Hydride Shift in the Biosynthesis of Pinguisane-type Sesquiterpenes. Bioscience, Biotechnology, and Biochemistry 1999, 63, 1667. <https://doi.org/10.1271/bbb.63.1667>
- Srikrishna A., Vijaykumar D.: Enantiospecific synthesis of (+)-pinguisenol, (+)-pinguisen-10-one and (−)-pinguisen-8,10-dione. Tetrahedron Letters 1998, 39, 4901. <https://doi.org/10.1016/S0040-4039(98)00891-0>
- Allen Angela J., Vaillancourt Valerie, Albizati Kim F.: FURANOSESQUITERPENE SYNTHESIS. AN UPDATED REVIEW. Organic Preparations and Procedures International 1994, 26, 1. <https://doi.org/10.1080/00304949409458014>
- Zinsmeister Hans Dietmar, Becker Hans, Eicher Theophil: Moose, eine Quelle biologisch aktiver Naturstoffe?. Angewandte Chemie 1991, 103, 134. <https://doi.org/10.1002/ange.19911030205>
- Zinsmeister Hans Dietmar, Becker Hans, Eicher Theophil: Bryophytes, a Source of Biologically Active, Naturally Occurring Material?. Angew. Chem. Int. Ed. Engl. 1991, 30, 130. <https://doi.org/10.1002/anie.199101301>
- Becker H.: Bryophytes, a Rich Source of Secondary Metabolites. Botanica Acta 1989, 102, 181. <https://doi.org/10.1111/j.1438-8677.1989.tb00090.x>
- Gambacorta A., Botta M., Turchetta S.: Bicyclo [3,3,1] nonane approach to pinguisane terpenoids. Tetrahedron 1988, 44, 4837. <https://doi.org/10.1016/S0040-4020(01)86187-1>
- Uyehara Tadao, Kabasawa Yasuhiro, Kato Tadahiro: Rearrangement Approaches to Cyclic Skeletons. IV. The Total Synthesis of (±)-Pinguisone and (±)-Deoxopinguisone Based on Photochemical [1,3] Acyl Migration of a Bicyclo[3.2.2]non-6-en-2-one. Bulletin of the Chemical Society of Japan 1986, 59, 2521. <https://doi.org/10.1246/bcsj.59.2521>
- Uyehara Tadao, Kabasawa Yasuhiro, Kato Tadahiro, Furuta Toshiaki: Photochemical rearrangement approach to the total synthesis of (±)-pinguisone and (±)-deoxopinguisone. Tetrahedron Letters 1985, 26, 2343. <https://doi.org/10.1016/S0040-4039(00)95094-9>
- Asakawa Yoshinori, Toyota Masao, Matsuda Reiko, Takikawa Keiko, Takemoto Tsunematsu: Distribution of novel cyclic bisbibenzyls in Marchantia and Riccardia species. Phytochemistry 1983, 22, 1413. <https://doi.org/10.1016/S0031-9422(00)84025-X>
- Takeda Reiji, Naoki Hideo, Iwashita Takashi, Mizukawa Kosei, Hirose Yoshio, Isida Toshimasa, Inoue Masatoshi: Sesquiterpenoid Constituents of the Liverwort, Ptychanthus striatus (LEhm. et LIndenb.) NEes. Bulletin of the Chemical Society of Japan 1983, 56, 1125. <https://doi.org/10.1246/bcsj.56.1125>
- Asakawa Yoshinori, Toyota Masao, Takeda Reiji, Suire Claude, Takemoto Tsunematsu: Sesquiterpenoids of Riccardia and Pallavicinia species. Phytochemistry 1981, 20, 725. <https://doi.org/10.1016/0031-9422(81)85161-8>
- Asakawa Yoshinori, Toyota Masao, Takemoto Tsunematsu, Mues Rudiger: Aromatic esters and terpenoids of the liverworts in the genera Trichocolea, Neotrichocolea and Trichocoleopsis. Phytochemistry 1981, 20, 2695. <https://doi.org/10.1016/0031-9422(81)85270-3>
- Bernasconi S., Gariboldi P., Jommi G., Sisti M.: C-acylation of enolates from lithium dimethylcuprate addition to α,β-unsaturated ketones. Tetrahedron Letters 1980, 21, 2337. <https://doi.org/10.1016/S0040-4039(00)92600-5>
- Asakawa Yoshinori, Toyota Masao, Takemoto Tsunematsu, Suire Claude: Pinguisanin, pinguisanolide and β-pinguisenediol, three new pinguisane-type sesquiterpenes from Porella platyphylla. Phytochemistry 1979, 18, 1349. <https://doi.org/10.1016/0031-9422(79)83020-4>
- Anderson Niels H., Ohta Yoshimoto, Moore Ana, Tseng Chia-Li W.: Anastreptene, a commonly encountered sesquiterpene of liverworts (hepaticae). Tetrahedron 1978, 34, 41. <https://doi.org/10.1016/0040-4020(78)88033-8>
- Asakawa Yoshinori, Tsunematsu Takemoto: Le diterpenoid du gout piquant de Pellia endiviaefolia. Phytochemistry 1978, 17, 153. <https://doi.org/10.1016/S0031-9422(00)89703-4>
- Andersen Neils H., Bissonette P., Liu C.-B., Shunk Belinda, Ohta Yoshimoto, Tseng Chia-Li W., Moore Ana, Huneck S.: Sesquiterpenes of nine european liverworts from the genera, Anastrepta, bazzania, jungermannia, lepidozia and Scapania. Phytochemistry 1977, 16, 1731. <https://doi.org/10.1016/0031-9422(71)85081-1>
- Ohta Yoshimoto, Andersen Niels H., Liu C.-B.: Sesquiterpene constituents of two liverworts of genus diplophyllum. Tetrahedron 1977, 33, 617. <https://doi.org/10.1016/0040-4020(77)80301-3>
- Asakawa Yoshinori, Takemoto Tsunematsu, Toyota Masao, Aratani Takaaki: Sacculatal and isosacculatal, two new exceptional diterpenedials from the liverwort, trichocoleopsis sacculata. Tetrahedron Letters 1977, 18, 1407. <https://doi.org/10.1016/S0040-4039(01)93057-6>
- Asakawa Yoshinori, Toyota Masao, Aratani Takaaki: Un nouvel alcool sesquiterpénique de et (hépatiques). Tetrahedron Letters 1976, 17, 3619. <https://doi.org/10.1016/S0040-4039(00)92976-9>
- Barnett B. L., Yordy J. D.: Crystal structure of (1R *,6S *,8R *,10R *)-8-(p-bromobenzensulfonoxy)-1,10-dimethyltricyclo [4.4.0.03,8]decan-2-one. Journal of Crystal and Molecular Structure 1975, 5, 113. <https://doi.org/10.1007/BF01387005>
- Krutov S.M., Samek Z., Benešova V., Herout V.: Isolation and the structure of deoxopinguisone from the liverwort Ptilidium ciliare. Phytochemistry 1973, 12, 1405. <https://doi.org/10.1016/0031-9422(73)80574-6>
- Benešová V., Minh Châu Hoang, Herout V.: Hepaticae. Phytochemistry 1973, 12, 211. <https://doi.org/10.1016/S0031-9422(00)84652-X>
- Matsuo Akihiko, Nakayama Mitsuru, Hayashi Shuichi: CHEMICAL PROOF OF ENANTIOMERIC (−)-LONGIBORNEOL. Chemistry Letters 1973, 2, 769. <https://doi.org/10.1246/cl.1973.769>
- Matsuo Akihiko, Nakayama Mitsuru, Hayashi Shûichi: Fatty acid esters in the volatile oil from the liverwort, Pellia fabbroniana. Phytochemistry 1971, 10, 430. <https://doi.org/10.1016/S0031-9422(00)94063-9>
- Matsuo A.: Structure of bazzanene. Tetrahedron 1971, 27, 2757. <https://doi.org/10.1016/S0040-4020(01)98065-2>
- Benešová V., Sedmera P., Herout V., Šorm F.: The structure of a tetracyclic sesquiterpenic alcohol from liverwort mylia taylorii (hook.) gray. Tetrahedron Letters 1971, 12, 2679. <https://doi.org/10.1016/S0040-4039(01)96950-3>