Literature DB >> 30319159

Synthesis and Study of the Antimalarial Cardamom Peroxide.

Xirui Hu1, Pharath Lim2,3, Rick M Fairhurst2, Thomas J Maimone1.   

Abstract

A full account of our previously disclosed synthesis of the monoterpene dimer cardamom peroxide is reported. Inspired by hypotheses regarding the potential biosynthetic origins of this natural product, several unproductive routes are also reported. The chemical reactivity of this structurally unique metabolite in the presence of iron(II) sources is also reported as is its antimalarial activity against Plasmodium falciparum clinical isolates from several Cambodian provinces.

Entities:  

Keywords:  endoperoxide; malaria; natural product; total synthesis

Year:  2018        PMID： 30319159      PMCID： PMC6181145          DOI： 10.1016/j.tet.2018.03.045

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  76 in total

1.  Total syntheses of guanacastepenes N and O.

Authors:  Christian M Gampe; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-02       Impact factor: 15.336

2.  Reductive olefination of aldehydes via chromium Brook rearrangement.

Authors:  Rachid Baati; Charles Mioskowski; Deb Barma; Rajashaker Kache; J R Falck
Journal:  Org Lett       Date:  2006-07-06       Impact factor: 6.005

3.  Fragmentation of β-hydroxy hydroperoxides.

Authors:  Xiaodong Gu; Wujuan Zhang; Robert G Salomon
Journal:  J Org Chem       Date:  2012-01-24       Impact factor: 4.354

4.  Mild TiIII- and Mn/ZrIV-catalytic reductive coupling of allylic halides: efficient synthesis of symmetric terpenes.

Authors:  Alejandro F Barrero; M Mar Herrador; José F Quílez del Moral; Pilar Arteaga; Jesús F Arteaga; Horacio R Diéguez; Elena M Sánchez
Journal:  J Org Chem       Date:  2007-03-22       Impact factor: 4.354

5.  Direct synthesis of 1,4-diols from alkenes by iron-catalyzed aerobic hydration and C-H hydroxylation.

Authors:  Takuma Hashimoto; Daisuke Hirose; Tsuyoshi Taniguchi
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-02       Impact factor: 15.336

6.  Hydroheteroarylation of Unactivated Alkenes Using N-Methoxyheteroarenium Salts.

Authors:  Xiaoshen Ma; Hester Dang; John A Rose; Paul Rablen; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2017-04-12       Impact factor: 15.419

7.  Identification of an antimalarial synthetic trioxolane drug development candidate.

Authors:  Jonathan L Vennerstrom; Sarah Arbe-Barnes; Reto Brun; Susan A Charman; Francis C K Chiu; Jacques Chollet; Yuxiang Dong; Arnulf Dorn; Daniel Hunziker; Hugues Matile; Kylie McIntosh; Maniyan Padmanilayam; Josefina Santo Tomas; Christian Scheurer; Bernard Scorneaux; Yuanqing Tang; Heinrich Urwyler; Sergio Wittlin; William N Charman
Journal:  Nature       Date:  2004-08-19       Impact factor: 49.962

8.  Artemisinin resistance in Plasmodium falciparum malaria.

Authors:  Arjen M Dondorp; François Nosten; Poravuth Yi; Debashish Das; Aung Phae Phyo; Joel Tarning; Khin Maung Lwin; Frederic Ariey; Warunee Hanpithakpong; Sue J Lee; Pascal Ringwald; Kamolrat Silamut; Mallika Imwong; Kesinee Chotivanich; Pharath Lim; Trent Herdman; Sen Sam An; Shunmay Yeung; Pratap Singhasivanon; Nicholas P J Day; Niklas Lindegardh; Duong Socheat; Nicholas J White
Journal:  N Engl J Med       Date:  2009-07-30       Impact factor: 91.245

9.  Spread of artemisinin resistance in Plasmodium falciparum malaria.

Authors:  Elizabeth A Ashley; Mehul Dhorda; Rick M Fairhurst; Chanaki Amaratunga; Parath Lim; Seila Suon; Sokunthea Sreng; Jennifer M Anderson; Sivanna Mao; Baramey Sam; Chantha Sopha; Char Meng Chuor; Chea Nguon; Siv Sovannaroth; Sasithon Pukrittayakamee; Podjanee Jittamala; Kesinee Chotivanich; Kitipumi Chutasmit; Chaiyaporn Suchatsoonthorn; Ratchadaporn Runcharoen; Tran Tinh Hien; Nguyen Thanh Thuy-Nhien; Ngo Viet Thanh; Nguyen Hoan Phu; Ye Htut; Kay-Thwe Han; Kyin Hla Aye; Olugbenga A Mokuolu; Rasaq R Olaosebikan; Olaleke O Folaranmi; Mayfong Mayxay; Maniphone Khanthavong; Bouasy Hongvanthong; Paul N Newton; Marie A Onyamboko; Caterina I Fanello; Antoinette K Tshefu; Neelima Mishra; Neena Valecha; Aung Pyae Phyo; Francois Nosten; Poravuth Yi; Rupam Tripura; Steffen Borrmann; Mahfudh Bashraheil; Judy Peshu; M Abul Faiz; Aniruddha Ghose; M Amir Hossain; Rasheda Samad; M Ridwanur Rahman; M Mahtabuddin Hasan; Akhterul Islam; Olivo Miotto; Roberto Amato; Bronwyn MacInnis; Jim Stalker; Dominic P Kwiatkowski; Zbynek Bozdech; Atthanee Jeeyapant; Phaik Yeong Cheah; Tharisara Sakulthaew; Jeremy Chalk; Benjamas Intharabut; Kamolrat Silamut; Sue J Lee; Benchawan Vihokhern; Chanon Kunasol; Mallika Imwong; Joel Tarning; Walter J Taylor; Shunmay Yeung; Charles J Woodrow; Jennifer A Flegg; Debashish Das; Jeffery Smith; Meera Venkatesan; Christopher V Plowe; Kasia Stepniewska; Philippe J Guerin; Arjen M Dondorp; Nicholas P Day; Nicholas J White
Journal:  N Engl J Med       Date:  2014-07-31       Impact factor: 91.245

10.  A novel multiple-stage antimalarial agent that inhibits protein synthesis.

Authors:  Beatriz Baragaña; Irene Hallyburton; Marcus C S Lee; Neil R Norcross; Raffaella Grimaldi; Thomas D Otto; William R Proto; Andrew M Blagborough; Stephan Meister; Grennady Wirjanata; Andrea Ruecker; Leanna M Upton; Tara S Abraham; Mariana J Almeida; Anupam Pradhan; Achim Porzelle; María Santos Martínez; Torsten Luksch; Judith M Bolscher; Andrew Woodland; Suzanne Norval; Fabio Zuccotto; John Thomas; Frederick Simeons; Laste Stojanovski; Maria Osuna-Cabello; Paddy M Brock; Tom S Churcher; Katarzyna A Sala; Sara E Zakutansky; María Belén Jiménez-Díaz; Laura Maria Sanz; Jennifer Riley; Rajshekhar Basak; Michael Campbell; Vicky M Avery; Robert W Sauerwein; Koen J Dechering; Rintis Noviyanti; Brice Campo; Julie A Frearson; Iñigo Angulo-Barturen; Santiago Ferrer-Bazaga; Francisco Javier Gamo; Paul G Wyatt; Didier Leroy; Peter Siegl; Michael J Delves; Dennis E Kyle; Sergio Wittlin; Jutta Marfurt; Ric N Price; Robert E Sinden; Elizabeth A Winzeler; Susan A Charman; Lidiya Bebrevska; David W Gray; Simon Campbell; Alan H Fairlamb; Paul A Willis; Julian C Rayner; David A Fidock; Kevin D Read; Ian H Gilbert
Journal:  Nature       Date:  2015-06-18       Impact factor: 49.962
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  3 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

Review 2.  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

3.  Evolution of a Synthetic Strategy for Complex Polypyrrole Alkaloids: Total Syntheses of Curvulamine and Curindolizine.

Authors:  Jun Xuan; Karl T Haelsig; Michael Sheremet; Paulo A Machicao; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2021-02-11       Impact factor: 15.419
  3 in total

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