Literature DB >> 24757120

An enantiospecific synthesis of jiadifenolide.

David A Siler1, Jeffrey D Mighion, Erik J Sorensen.   

Abstract

A Robinson annulation, van Leusen homologation, and a desymmetrizing C-H oxidation enabled an enantiospecific synthesis of the neurotrophic natural product jiadifenolide. From a pulegone-derived building block, a key propellane intermediate was constructed through the use of simple reagents in a highly diastereoselective fashion. A short series of oxidations of this tricylic framework allowed progression to the natural product.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; chiral pool; natural products; terpenoids; total synthesis

Mesh：

Substances：

Year:  2014        PMID： 24757120      PMCID： PMC4153357          DOI： 10.1002/anie.201402335

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


  15 in total

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Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
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8.  Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; William C Mobley; Emmanuel A Theodorakis
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Review 9.  Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

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  13 in total

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Authors:  Hai-Hua Lu; Michael D Martinez; Ryan A Shenvi
Journal:  Nat Chem       Date:  2015-06-15       Impact factor: 24.427

Review 2.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

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Authors:  Robert J Sharpe; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

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Authors:  Robert J Sharpe; Jeffrey S Johnson
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6.  Local Desymmetrization through Diastereotopic Group Selection: An Enabling Strategy for Natural Product Synthesis.

Authors:  Matthew A Horwitz; Jeffrey S Johnson
Journal:  European J Org Chem       Date:  2017-02-07

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

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

Authors:  Matthew L Condakes; Luiz F T Novaes; Thomas J Maimone
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9.  Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.

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10.  Total Synthesis of (-)-Maximiscin.

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Journal:  J Am Chem Soc       Date:  2020-05-01       Impact factor: 15.419
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