Literature DB >> 31329434

A Radical-Polar Crossover Annulation To Access Terpenoid Motifs.

William P Thomas1, Devon J Schatz1, David T George1, Sergey V Pronin1.   

Abstract

A new catalytic radical-polar crossover annulation between two unsaturated carbonyl compounds is described. The annulation proceeds under exceptionally mild conditions and provides direct and expedient access to complex terpenoid motifs. Application of this chemistry allows for synthesis of forskolin, a densely functionalized terpenoid, in 14 steps from commercially available material.

Entities:  

Year:  2019        PMID: 31329434     DOI: 10.1021/jacs.9b07346

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  5 in total

1.  Enantiospecific Entry to a Common Decalin Intermediate for the Syntheses of Highly Oxygenated Terpenoids.

Authors:  Shota Nagasawa; Kerry E Jones; Richmond Sarpong
Journal:  J Org Chem       Date:  2019-09-11       Impact factor: 4.354

2.  Generation of α-Boryl Radicals by H. Transfer and their Use in Cycloisomerizations.

Authors:  Shicheng Shi; Farbod Salahi; Hunter B Vibbert; Maleeha Rahman; Scott A Snyder; Jack R Norton
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-15       Impact factor: 16.823

3.  Catalytic Cycloisomerization onto a Carbonyl Oxygen.

Authors:  Shicheng Shi; Jonathan L Kuo; Tao Chen; Jack R Norton
Journal:  Org Lett       Date:  2020-07-22       Impact factor: 6.005

4.  Stereocontrolled Radical Bicyclizations of Oxygenated Precursors Enable Short Syntheses of Oxidized Abietane Diterpenoids.

Authors:  Darius Vrubliauskas; Benjamin M Gross; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2021-02-08       Impact factor: 15.419

Review 5.  Reductive radical-polar crossover: traditional electrophiles in modern radical reactions.

Authors:  Lena Pitzer; J Luca Schwarz; Frank Glorius
Journal:  Chem Sci       Date:  2019-08-16       Impact factor: 9.825

  5 in total

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