Literature DB >> 25470723

Short, enantioselective total synthesis of chatancin.

Yu-Ming Zhao1, Thomas J Maimone.   

Abstract

An enantioselective total synthesis of the polycyclic diterpene (+)-chatancin, a potent PAF antagonist, is reported. Proceeding in seven steps from dihydrofarnesal, this synthetic route was designed to circumvent macrocyclization-based strategies to complex, cyclized cembranoids. The described synthesis requires only six chromatographic purifications, is high yielding, and avoids protecting-group manipulations. An X-ray crystal structure of this fragile marine natural product was obtained.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric synthesis; biomimetic synthesis; cycloaddition reaction; natural products; terpenes

Mesh：

Substances：

Year:  2014        PMID： 25470723      PMCID： PMC4300267          DOI： 10.1002/anie.201410443

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  36 in total

Review 1.  Highlights of marine invertebrate-derived biosynthetic products: their biomedical potential and possible production by microbial associants.

Authors:  Ocky K Radjasa; Yvette M Vaske; Gabriel Navarro; Hélène C Vervoort; Karen Tenney; Roger G Linington; Phillip Crews
Journal:  Bioorg Med Chem       Date:  2011-07-26       Impact factor: 3.641

2.  Exploring biosynthetic relationships among furanocembranoids: synthesis of (-)-bipinnatin J, (+)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B.

Authors:  Paul A Roethle; Paul T Hernandez; Dirk Trauner
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

3.  Expedient synthesis of (+/-)-bipinnatin J.

Authors:  Paul A Roethle; Dirk Trauner
Journal:  Org Lett       Date:  2006-01-19       Impact factor: 6.005

Review 4.  Platelet-activating factor and related lipid mediators.

Authors:  S M Prescott; G A Zimmerman; D M Stafforini; T M McIntyre
Journal:  Annu Rev Biochem       Date:  2000       Impact factor: 23.643

5.  Pyranophane transannular diels-alder approach to (+)-chatancin: a biomimetic asymmetric total synthesis.

Authors:  Pierre Soucy; Alexandre L'Heureux; András Toró; Pierre Deslongchamps
Journal:  J Org Chem       Date:  2003-12-26       Impact factor: 4.354

6.  Biomimetic synthesis toward the transtaganolides/basiliolides.

Authors:  Rikard Larsson; Olov Sterner; Martin Johansson
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

7.  Total syntheses of (-)-transtaganolide A, (+)-transtaganolide B, (+)-transtaganolide C, and (-)-transtaganolide D and biosynthetic implications.

Authors:  Hosea M Nelson; Jonny R Gordon; Scott C Virgil; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-16       Impact factor: 15.336

8.  A concise total synthesis of (+)-scholarisine A empowered by a unique C-H arylation.

Authors:  Myles W Smith; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2013-08-21       Impact factor: 15.419

9.  The total syntheses of basiliolide C, epi-basiliolide C, and protecting-group-free total syntheses of transtaganolides C and D.

Authors:  Jonny R Gordon; Hosea M Nelson; Scott C Virgil; Brian M Stoltz
Journal:  J Org Chem       Date:  2014-10-06       Impact factor: 4.354

10.  Trends in the discovery of new marine natural products from invertebrates over the last two decades--where and what are we bioprospecting?

Authors:  Miguel Costa Leal; João Puga; João Serôdio; Newton C M Gomes; Ricardo Calado
Journal:  PLoS One       Date:  2012-01-20       Impact factor: 3.240
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  5 in total

1.  Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae.

Authors:  Xirui Hu; Andrew J Musacchio; Xingyu Shen; Yujia Tao; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

2.  Enantioselective synthesis of an ophiobolin sesterterpene via a programmed radical cascade.

Authors:  Zachary G Brill; Huck K Grover; Thomas J Maimone
Journal:  Science       Date:  2016-05-27       Impact factor: 47.728

Review 3.  Syntheses of Complex Terpenes from Simple Polyprenyl Precursors.

Authors:  Claire S Harmange Magnani; Danny Q Thach; Karl T Haelsig; Thomas J Maimone
Journal:  Acc Chem Res       Date:  2020-03-23       Impact factor: 22.384

4.  Novel, male-produced aggregation pheromone of the cerambycid beetle Rosalia alpina, a priority species of European conservation concern.

Authors:  Alenka Žunič Kosi; Yunfan Zou; Michal Hoskovec; Al Vrezec; Nataša Stritih; Jocelyn G Millar
Journal:  PLoS One       Date:  2017-08-21       Impact factor: 3.240

5.  An efficient approach to angular tricyclic molecular architecture via Nazarov-like cyclization and double ring-expansion cascade.

Authors:  Yun-Peng Wang; Kun Fang; Yong-Qiang Tu; Jun-Jie Yin; Qi Zhao; Tian Ke
Journal:  Nat Commun       Date:  2022-04-28       Impact factor: 17.694
  5 in total

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