Literature DB >> 19140719

Biomimetic synthesis toward the transtaganolides/basiliolides.

Rikard Larsson1, Olov Sterner, Martin Johansson.   

Abstract

A concise biomimetic approach toward transtaganolides C and D involving an Ireland-Claisen rearrangement/intramolecular Diels-Alder reaction sequence suggesting the involvement of pericyclic reactions in the biosynthesis of these biologically active plant metabolites is presented. A final coupling reaction establishes the carbon framework of the transtaganolides.

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Year:  2009        PMID： 19140719     DOI： 10.1021/ol802760z

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


  6 in total

Review 1.  Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

2.  Short, enantioselective total synthesis of chatancin.

Authors:  Yu-Ming Zhao; Thomas J Maimone
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-02       Impact factor: 15.336

3.  From Plant to Patient: Thapsigargin, a Tool for Understanding Natural Product Chemistry, Total Syntheses, Biosynthesis, Taxonomy, ATPases, Cell Death, and Drug Development.

Authors:  Søren Brøgger Christensen; Henrik Toft Simonsen; Nikolai Engedal; Poul Nissen; Jesper Vuust Møller; Samuel R Denmeade; John T Isaacs
Journal:  Prog Chem Org Nat Prod       Date:  2021

4.  Total syntheses of (-)-transtaganolide A, (+)-transtaganolide B, (+)-transtaganolide C, and (-)-transtaganolide D and biosynthetic implications.

Authors:  Hosea M Nelson; Jonny R Gordon; Scott C Virgil; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-16       Impact factor: 15.336

5.  Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones.

Authors:  Matam Parameshwar; Manda Rajesh; Sridhar Balasubramanian; Maddi Sridhar Reddy
Journal:  ACS Omega       Date:  2019-10-30

Review 6.  Assessment on facile Diels-Alder approach of α-pyrone and terpenoquinone for the expedient synthesis of various natural scaffolds.

Authors:  Aluru Rammohan; Albert F Khasanov; Dmitry S Kopchuk; Duvvuru Gunasekar; Grigory V Zyryanov; Oleg N Chupakhin
Journal:  Nat Prod Bioprospect       Date:  2022-03-31
  6 in total

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