Literature DB >> 28696715

Approach to the Synthesis of Briarane Diterpenes through a Dianionic Claisen Rearrangement and Ring-Closing Metathesis.

Michael T Crimmins1, Yan Zhang1, Philip S Williams1.   

Abstract

The synthesis of the briarane-brianthein A core has been accomplished utilizing an extension of the dianionic Ireland-Claisen rearrangement to establish the C1 quaternary carbon and the adjacent C10 ring juncture stereocenters. Two sequential ring-closing metathesis reactions were exploited to construct the 6-10 trans fused ring system.

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Year:  2017        PMID： 28696715     DOI： 10.1021/acs.orglett.7b01806

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

Review 1.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

2.  Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids.

Authors:  Tyler J Fulton; Alexander Q Cusumano; Eric J Alexy; Yun E Du; Haiming Zhang; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2020-12-15       Impact factor: 15.419

3.  Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.

Authors:  Kaushalendra Patel; Veeranjaneyulu Lanke; Ilan Marek
Journal:  J Am Chem Soc       Date:  2022-04-12       Impact factor: 16.383

Review 4.  Synthetic explorations of the briarane jungle: progress in developing a synthetic route to a common family of diterpenoid natural products.

Authors:  Nicholas G Moon; Andrew M Harned
Journal:  R Soc Open Sci       Date:  2018-05-23       Impact factor: 2.963
  4 in total

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