Literature DB >> 30525614

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

Matthew L Condakes1, Luiz F T Novaes1, Thomas J Maimone1.   

Abstract

Since the elucidation of the structure of anisatin in the late 1960s, sesquiterpene lactones from various Illicium species of plants have captivated synthetic chemists worldwide, resulting in a large body of synthetic work. In particular, Illicium sesquiterpenes containing the seco-prezizaane carbon framework have seen immense interest in recent years owing to desirable structural and medicinal attributes. This synopsis will focus on recently developed synthetic strategies to access these compact, highly oxidized terpenoids.

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Year:  2018        PMID: 30525614      PMCID: PMC6467809          DOI: 10.1021/acs.joc.8b02802

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  44 in total

1.  Formal synthesis of merrilactone A using a domino cyanide 1,4-addition-aldol cyclization.

Authors:  Naim Nazef; Robert D M Davies; Michael F Greaney
Journal:  Org Lett       Date:  2012-07-09       Impact factor: 6.005

2.  Synthetic studies toward anisatin: a formal synthesis of (+/-)-8-deoxyanisatin.

Authors:  T P Loh; Q Y Hu
Journal:  Org Lett       Date:  2001-01-25       Impact factor: 6.005

3.  Total synthesis of (-)-anisatin.

Authors:  Akihiro Ogura; Kohei Yamada; Satoshi Yokoshima; Tohru Fukuyama
Journal:  Org Lett       Date:  2012-02-28       Impact factor: 6.005

4.  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

5.  Total Syntheses of Scaparvins B, C, and D Enabled by a Key C-H Functionalization.

Authors:  Qinda Ye; Pei Qu; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2017-12-11       Impact factor: 15.419

6.  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

7.  Total synthesis of (+/-)-jiadifenin, a non-peptidyl neurotrophic modulator.

Authors:  Young Shin Cho; David A Carcache; Yuan Tian; Yue-Ming Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2004-11-10       Impact factor: 15.419

8.  Interaction of anisatin with rat brain gamma-aminobutyric acidA receptors: allosteric modulation by competitive antagonists.

Authors:  E Kakemoto; E Okuyama; K Nagata; Y Ozoe
Journal:  Biochem Pharmacol       Date:  1999-08-15       Impact factor: 5.858

9.  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

10.  Total Syntheses of (-)-Majucin and (-)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes.

Authors:  Matthew L Condakes; Kevin Hung; Stephen J Harwood; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2017-11-26       Impact factor: 15.419

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  4 in total

1.  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

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

Review 3.  An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

Authors:  Alexander W Schuppe; Yannan Liu; Timothy R Newhouse
Journal:  Nat Prod Rep       Date:  2020-09-15       Impact factor: 13.423

4.  Bioavailability and Pharmacokinetics of Anisatin in Mouse Blood by Ultra-Performance Liquid Chromatography-Tandem Mass Spectrometry.

Authors:  Xi Bao; Xiajuan Jiang; Jianshe Ma; Xianqin Wang; Quan Zhou
Journal:  Biomed Res Int       Date:  2020-12-23       Impact factor: 3.411

  4 in total

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