Literature DB >> 28379015

Tricyclic Sesquiterpenes from Marine Origin.

Franck Le Bideau1, Mohammad Kousara1,2, Li Chen1, Lai Wei1, Françoise Dumas1.   

Abstract

The structure elucidation, biosynthesis, and biological activity of marine carbotricyclic sesquiterpene compounds are reviewed from the pioneering results to the end of 2015. Their total syntheses with a particular emphasis on the first syntheses, enantiomeric versions, and syntheses that led to the revision of structures or stereochemistries are summarized. Overall, 284 tricyclic compounds are classified into fused, bridged, and miscellaneous structures based on 54 different skeletal types. Tricyclic sesquiterpenes constitute an important group of natural products. Their structural diversity and biological activities have generated further interest in the field of drug discovery research, although the exact mechanisms of action of these species are not well known. Furthermore, these tricyclic structures, according to their chemical complexity, are a source of inspiration for chemists in the field of total synthesis for the development of innovative methodologies.

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Year:  2017        PMID: 28379015     DOI: 10.1021/acs.chemrev.6b00502

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  16 in total

1.  Computational and Synthetic Investigation of Cationic Rearrangement in the Putative Biosynthesis of Justicane Triterpenoids.

Authors:  Masha Elkin; Anthony C Scruse; Aneta Turlik; Timothy R Newhouse
Journal:  Angew Chem Int Ed Engl       Date:  2018-12-21       Impact factor: 15.336

2.  Diols as Dienophiles: Bridged Carbocycles via Ruthenium(0)-Catalyzed Transfer Hydrogenative Cycloadditions of Cyclohexadiene or Norbornadiene.

Authors:  Hiroki Sato; Keisuke Fukaya; Binit Sharma Poudel; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-10       Impact factor: 15.336

3.  Phytochemical study of the headspace volatile organic compounds of fresh algae and seagrass from the Adriatic Sea (single point collection).

Authors:  Igor Jerković; Zvonimir Marijanović; Marin Roje; Piotr M Kuś; Stela Jokić; Rozelinda Čož-Rakovac
Journal:  PLoS One       Date:  2018-05-08       Impact factor: 3.240

4.  Antartin, a Cytotoxic Zizaane-Type Sesquiterpenoid from a Streptomyces sp. Isolated from an Antarctic Marine Sediment.

Authors:  Dayoung Kim; Eun Ju Lee; Jihye Lee; Alain S Leutou; Yern-Hyerk Shin; Bomi Choi; Ji Sun Hwang; Dongyup Hahn; Hyukjae Choi; Jungwook Chin; Sung Jin Cho; Yong Deog Hong; Jaeyoung Ko; Chi Nam Seong; Katherine N Maloney; Dong-Chan Oh; Inho Yang; Hayoung Hwang; Sang-Jip Nam
Journal:  Mar Drugs       Date:  2018-04-16       Impact factor: 5.118

5.  Total synthesis of avenaol.

Authors:  Motohiro Yasui; Rina Ota; Chihiro Tsukano; Yoshiji Takemoto
Journal:  Nat Commun       Date:  2017-09-22       Impact factor: 14.919

Review 6.  Linear Triquinane Sesquiterpenoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis.

Authors:  Yi Qiu; Wen-Jian Lan; Hou-Jin Li; Liu-Ping Chen
Journal:  Molecules       Date:  2018-08-21       Impact factor: 4.411

7.  Switchable selectivity in Pd-catalyzed [3 + 2] annulations of γ-oxy-2-cycloalkenones with 3-oxoglutarates: C-C/C-C vs C-C/O-C bond formation.

Authors:  Yang Liu; Julie Oble; Giovanni Poli
Journal:  Beilstein J Org Chem       Date:  2019-05-16       Impact factor: 2.883

8.  Peyssonnosides A-B, Unusual Diterpene Glycosides with a Sterically Encumbered Cyclopropane Motif: Structure Elucidation Using an Integrated Spectroscopic and Computational Workflow.

Authors:  Bhuwan Khatri Chhetri; Serge Lavoie; Anne Marie Sweeney-Jones; Nazia Mojib; Vijay Raghavan; Kerstin Gagaring; Brandon Dale; Case W McNamara; Katy Soapi; Cassandra L Quave; Prasad L Polavarapu; Julia Kubanek
Journal:  J Org Chem       Date:  2019-06-18       Impact factor: 4.354

Review 9.  Marine Terpenoids from Polar Latitudes and Their Potential Applications in Biotechnology.

Authors:  Laura Núñez-Pons; Andrew Shilling; Cinzia Verde; Bill J Baker; Daniela Giordano
Journal:  Mar Drugs       Date:  2020-07-29       Impact factor: 5.118

10.  Chemical Diversity of Headspace and Volatile Oil Composition of Two Brown Algae (Taonia atomaria and Padina pavonica) from the Adriatic Sea.

Authors:  Igor Jerković; Marina Kranjac; Zvonimir Marijanović; Marin Roje; Stela Jokić
Journal:  Molecules       Date:  2019-01-30       Impact factor: 4.411

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