Literature DB >> 28510286

An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Readily Available Starting Materials.

Sarah K Scott1, Alexander J Grenning1.   

Abstract

Cyclohexanone-derived Knoevenagel adducts (cyclohexylidenemalononitriles) and two different propargyl electrophiles serve as carbon sources for assembling diverse 6/7/5 tricycloalkanes, a common terpenoid framework. The sequence involves three unique reactions: 1) deconjugative propargylation, 2) one-pot enyne Cope rearrangement/deconjugative propargylation, and 3) an allenic Pauson-Khand reaction.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allenes; cyclization; rearrangements; rhodium; terpenoids

Year:  2017        PMID： 28510286     DOI： 10.1002/anie.201703186

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


  3 in total

1.  Overcoming Kinetic and Thermodynamic Challenges of Classic Cope Rearrangements.

Authors:  Ehsan Fereyduni; Ouidad Lahtigui; Jacob N Sanders; Breanna M Tomiczek; Michael D Mannchen; Roland A Yu; K N Houk; Alexander J Grenning
Journal:  J Org Chem       Date:  2021-01-21       Impact factor: 4.354

2.  Function-Oriented and Modular (+/-)-cis-Pseudoguaianolide Synthesis: Discovery of New Nrf2 Activators and NF-κB Inhibitors.

Authors:  Fabien Emmetiere; Ranjala Ratnayake; Henry A M Schares; Katherine F M Jones; Emily Bevan-Smith; Hendrik Luesch; Daniel A Harki; Alexander J Grenning
Journal:  Chemistry       Date:  2021-02-26       Impact factor: 5.236

3.  Controlling, Understanding, and Redirecting the Thermal Rearrangement of 3,3-Dicyano-1,5-enynes.

Authors:  Sarah K Scott; Jacob N Sanders; Katherine E White; Roland A Yu; K N Houk; Alexander J Grenning
Journal:  J Am Chem Soc       Date:  2018-11-12       Impact factor: 15.419
  3 in total

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