Literature DB >> 24867775

Biomimetic synthesis of (+)-ledene, (+)-viridiflorol, (-)-palustrol, (+)-spathulenol, and psiguadial A, C, and D via the platform terpene (+)-bicyclogermacrene.

Duc N Tran1, Nicolai Cramer.   

Abstract

(+)-Bicyclogermacrene is a strained bicyclic and common sesquiterpene found in several essential oils. A short and good yielding synthesis of bicyclogermacrene proceeding in seven steps is reported. This terpene is used as key platform intermediate for a biomimetic access to several aromadendrene sesquiterpenoids, such as ledene, viridiflorol, palestrol, and spathulenol. Furthermore, bicyclogermacrene is shown to be the terpene component in the synthesis of the meroterpenoids psiguadial A, C, and D.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  bicyclogermacrene; biomimetic synthesis; cyclization; natural products; terpenes

Mesh:

Substances:

Year:  2014        PMID: 24867775     DOI: 10.1002/chem.201403082

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  8 in total

Review 1.  Biological activities of meroterpenoids isolated from different sources.

Authors:  Neeraj Kumar Fuloria; Radhika K Raheja; Kaushal H Shah; Manisha J Oza; Yogesh A Kulkarni; Vetriselvan Subramaniyan; Mahendran Sekar; Shivkanya Fuloria
Journal:  Front Pharmacol       Date:  2022-09-19       Impact factor: 5.988

2.  Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B.

Authors:  Lauren M Chapman; Jordan C Beck; Caitlin R Lacker; Linglin Wu; Sarah E Reisman
Journal:  J Org Chem       Date:  2018-05-18       Impact factor: 4.354

3.  Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Authors:  Steven W M Crossley; Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  Chem Rev       Date:  2016-07-27       Impact factor: 60.622

4.  Cytotoxic Meroterpenoids with Rare Skeletons from Psidium guajava Cultivated in Temperate Zone.

Authors:  Xu-Jie Qin; Huan Yan; Wei Ni; Mu-Yuan Yu; Afsar Khan; Hui Liu; Hong-Xia Zhang; Li He; Xiao-Jiang Hao; Ying-Tong Di; Hai-Yang Liu
Journal:  Sci Rep       Date:  2016-09-02       Impact factor: 4.379

5.  New Formyl Phloroglucinol Meroterpenoids from the Leaves of Eucalyptus robusta.

Authors:  Zhi-Chun Shang; Ming-Hua Yang; Rui-Huan Liu; Xiao-Bing Wang; Ling-Yi Kong
Journal:  Sci Rep       Date:  2016-12-22       Impact factor: 4.379

6.  Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes.

Authors:  Anup Bhunia; Klaus Bergander; Constantin Gabriel Daniliuc; Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-03       Impact factor: 15.336

7.  Psiguajadials A-K: Unusual Psidium Meroterpenoids as Phosphodiesterase-4 Inhibitors from the Leaves of Psidium guajava.

Authors:  Gui-Hua Tang; Zhen Dong; Yan-Qiong Guo; Zhong-Bin Cheng; Chu-Jun Zhou; Sheng Yin
Journal:  Sci Rep       Date:  2017-04-21       Impact factor: 4.379

8.  Toxic, Radical Scavenging, and Antifungal Activity of Rhododendron tomentosum H. Essential Oils.

Authors:  Asta Judzentiene; Jurga Budiene; Jurgita Svediene; Rasa Garjonyte
Journal:  Molecules       Date:  2020-04-05       Impact factor: 4.411

  8 in total

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