Literature DB >> 20235528

A short biomimetic synthesis of the meroterpenoids guajadial and psidial A.

Andrew L Lawrence1, Robert M Adlington, Jack E Baldwin, Victor Lee, Jessica A Kershaw, Amber L Thompson.   

Abstract

The biosynthesis of the meroterpenoid guajadial was previously hypothesized to occur via a hetero-Diels-Alder reaction between caryophyllene and an o-quinone methide. This hypothesis has been verified via the biomimetic synthesis of guajadial and psidial A in an aqueous three-component coupling reaction, between caryophyllene, benzaldehyde, and diformylphloroglucinol.

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Year:  2010        PMID： 20235528     DOI： 10.1021/ol100138k

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


  12 in total

Review 1.  Peculiarities of meroterpenoids and their bioproduction.

Authors:  Jianying Han; Lan Jiang; Lixin Zhang; Ronald J Quinn; Xueting Liu; Yunjiang Feng
Journal:  Appl Microbiol Biotechnol       Date:  2021-05-03       Impact factor: 4.813

2.  Gold(I)-Mediated Cycloisomerization/Cycloaddition Enables Bioinspired Syntheses of Neonectrolides B-E and Analogues.

Authors:  Thomas J Purgett; Matthew W Dyer; Bryce Bickel; James McNeely; John A Porco
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

Review 3.  Recent advances in the synthesis of gem-dimethylcyclobutane natural products.

Authors:  Erin N Hancock; Johannes M Wiest; M Kevin Brown
Journal:  Nat Prod Rep       Date:  2019-10-16       Impact factor: 13.423

Review 4.  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

5.  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

6.  Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.

Authors:  Keith S Barbato; Yi Luan; Daniele Ramella; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2015-11-18       Impact factor: 6.005

7.  Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

Authors:  Yi Luan; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2012-12-03       Impact factor: 15.419

8.  Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate.

Authors:  Xu-Jie Qin; Tyler J Rauwolf; Pan-Pan Li; Hui Liu; James McNeely; Yan Hua; Hai-Yang Liu; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-20       Impact factor: 15.336

9.  Eucalyptusdimers A-C, Dimeric Phloroglucinol-Phellandrene Meroterpenoids from Eucalyptus robusta.

Authors:  Xu-Jie Qin; Mi-Yan Feng; Hui Liu; Wei Ni; Tyler Rauwolf; John A Porco; Huan Yan; Li He; Hai-Yang Liu
Journal:  Org Lett       Date:  2018-08-08       Impact factor: 6.005

Review 10.  Bioorthogonal chemistry: strategies and recent developments.

Authors:  Carlo P Ramil; Qing Lin
Journal:  Chem Commun (Camb)       Date:  2013-12-07       Impact factor: 6.222
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