Literature DB >> 26100810

An eight-step gram-scale synthesis of (-)-jiadifenolide.

Hai-Hua Lu1, Michael D Martinez1, Ryan A Shenvi1.   

Abstract

Development of a biologically active secondary metabolite into a useful medicine requires continuous access to meaningful quantities of material. Although any chemical synthesis is broadly useful for its versatility, identification of a synthesis route that can be economically scaled represents a greater challenge. Here we report a concise synthesis of the neurotrophic trace metabolite (-)-jiadifenolide and its production on a gram-scale. The brevity of the route and the structural similarity of a key intermediate to many potent Illicium terpenes make chemical synthesis the unquestionable method for accessing and modifying these potential therapeutics.

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Year:  2015        PMID: 26100810     DOI: 10.1038/nchem.2283

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  20 in total

1.  Butenolide synthesis by molybdenum-mediated hetero-pauson-khand reaction of alkynyl aldehydes.

Authors:  Javier Adrio; Juan C Carretero
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

2.  Total synthesis of (±)-merrilactone A.

Authors:  Jianwei Chen; Peng Gao; Fangmiao Yu; Yang Yang; Shizheng Zhu; Hongbin Zhai
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-04       Impact factor: 15.336

Review 3.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

4.  Total synthesis of (+/-)-jiadifenin and studies directed to understanding its SAR: probing mechanistic and stereochemical issues in palladium-mediated allylation of enolate-like structures.

Authors:  David A Carcache; Young Shin Cho; Zihao Hua; Yuan Tian; Yue-Ming Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

5.  An enantiospecific synthesis of jiadifenolide.

Authors:  David A Siler; Jeffrey D Mighion; Erik J Sorensen
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-23       Impact factor: 15.336

6.  Applications of total synthesis to problems in neurodegeneration: Fascinating chemistry along the way.

Authors:  Rebecca M Wilson; Samuel J Danishefsky
Journal:  Acc Chem Res       Date:  2006-08       Impact factor: 22.384

7.  Highly effective vinylogous Mukaiyama-Michael reaction catalyzed by silyl methide species generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane.

Authors:  Arata Takahashi; Hikaru Yanai; Min Zhang; Takaaki Sonoda; Masaaki Mishima; Takeo Taguchi
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

8.  Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; William C Mobley; Emmanuel A Theodorakis
Journal:  Chemistry       Date:  2013-03-22       Impact factor: 5.236

9.  Scope and facial selectivity of the Prins-pinacol synthesis of attached rings.

Authors:  Larry E Overman; Emile J Velthuisen
Journal:  J Org Chem       Date:  2006-02-17       Impact factor: 4.354

10.  Total synthesis of jiadifenolide.

Authors:  Ian Paterson; Mengyang Xuan; Stephen M Dalby
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-23       Impact factor: 15.336

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  20 in total

Review 1.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

2.  Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

Authors:  Kevin Hung; Matthew L Condakes; Luiz F T Novaes; Stephen J Harwood; Takahiro Morikawa; Zhi Yang; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2019-02-11       Impact factor: 15.419

3.  Pharmacological characterization of the neurotrophic sesquiterpene jiadifenolide reveals a non-convulsant signature and potential for progression in neurodegenerative disease studies.

Authors:  Jeffrey M Witkin; Ryan A Shenvi; Xia Li; Scott D Gleason; Julie Weiss; Denise Morrow; John T Catow; Mark Wakulchik; Masaki Ohtawa; Hai-Hua Lu; Michael D Martinez; Jeffrey M Schkeryantz; Timothy S Carpenter; Felice C Lightstone; Rok Cerne
Journal:  Biochem Pharmacol       Date:  2018-06-22       Impact factor: 5.858

4.  Synthesis of Neurotrophic Seco-prezizaane Sesquiterpenes (1R,10S)-2-Oxo-3,4-dehydroneomajucin, (2S)-Hydroxy-3,4-dehydroneomajucin, and (-)-Jiadifenin.

Authors:  Xiayun Cheng; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2016-01-25       Impact factor: 15.419

5.  Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation.

Authors:  Steven W M Crossley; Guanghu Tong; Michael J Lambrecht; Hannah E Burdge; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2020-06-23       Impact factor: 15.419

6.  Contemporary Synthetic Strategies toward seco-Prezizaane Sesquiterpenes from Illicium Species.

Authors:  Matthew L Condakes; Luiz F T Novaes; Thomas J Maimone
Journal:  J Org Chem       Date:  2018-12-07       Impact factor: 4.354

7.  Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.

Authors:  Kevin Hung; Matthew L Condakes; Takahiro Morikawa; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2016-12-16       Impact factor: 15.419

8.  A 15-step synthesis of (+)-ryanodol.

Authors:  Kangway V Chuang; Chen Xu; Sarah E Reisman
Journal:  Science       Date:  2016-08-26       Impact factor: 47.728

9.  Synthetic, Mechanistic, and Biological Interrogation of Ginkgo biloba Chemical Space En Route to (-)-Bilobalide.

Authors:  Robert M Demoret; Meghan A Baker; Masaki Ohtawa; Shuming Chen; Ching Ching Lam; Sophia Khom; Marisa Roberto; Stefano Forli; Kendall N Houk; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2020-10-16       Impact factor: 15.419

10.  Enantioselective Total Synthesis of Andrographolide and 14-Hydroxy-Colladonin: Carbonyl Reductive Coupling and trans-Decalin Formation by Hydrogen Transfer.

Authors:  Lin Yang; Thomas Wurm; Binit Sharma Poudel; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2020-10-15       Impact factor: 15.336

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