Literature DB >> 23721415

Biomimetic epoxide-opening cascades of oxasqualenoids triggered by hydrolysis of the terminal epoxide.

Yoshiki Morimoto1, Eriko Takeuchi, Hitomi Kambara, Takeshi Kodama, Yoshimitsu Tachi, Keisuke Nishikawa.   

Abstract

The biomimetic epoxide-opening cascades from squalene polyepoxides 4-6 to triterpene polyethers (oxasqualenoids) teurilene (1), glabrescol (2), and omaezakianol (3), respectively, were reproduced in a single event by chemical reaction. These cascades proceeded through the 5-exo tandem cyclization triggered by Brønsted acid-catalyzed hydrolysis of the terminal epoxide, mimicking the direct hydrolysis mechanism of epoxide hydrolases.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23721415     DOI： 10.1021/ol401081e

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

1.  Synthesis and biological analysis of truncated calyculone H.

Authors:  Penagaluri Balasubramanyam; Abimael D Rodríguez
Journal:  Tetrahedron       Date:  2017-01-14       Impact factor: 2.457

2.  Asymmetric Total Syntheses, Stereostructures, and Cytotoxicities of Marine Bromotriterpenoids Aplysiol B (Laurenmariannol) and Saiyacenol A.

Authors:  Kento Nishikibe; Keisuke Nishikawa; Momochika Kumagai; Matsumi Doe; Yoshiki Morimoto
Journal:  Chem Asian J       Date:  2021-11-16

3.  Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines.

Authors:  Eric Buchy; Branko Vukosavljevic; Maike Windbergs; Dunja Sobot; Camille Dejean; Simona Mura; Patrick Couvreur; Didier Desmaële
Journal:  Beilstein J Org Chem       Date:  2016-06-06       Impact factor: 2.883

Review 4.  The direct oxidative diene cyclization and related reactions in natural product synthesis.

Authors:  Juliane Adrian; Leona J Gross; Christian B W Stark
Journal:  Beilstein J Org Chem       Date:  2016-09-30       Impact factor: 2.883
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.