Literature DB >> 12599474

Highly selective entry to the azadirachtin skeleton via a Claisen rearrangement/radical cyclization sequence.

Thomas Durand-Reville1, Luca B Gobbi, Brian Lawrence Gray, Steven V Ley, James S Scott.   

Abstract

[formula: see text] A highly diastereoselective, microwave-induced Claisen rearrangement of an appropriately substituted propargylic enol ether allows the formation of the sterically congested C8-C14 bond of azadirachtin. When combined with a radical-mediated cyclization of the corresponding allene, this sequence offers rapid entry to the framework of azadirachtin.

Entities:  

Year:  2002        PMID： 12599474     DOI： 10.1021/ol0201557

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


  6 in total

1.  Total synthesis of atrochamins F, H, I, and J through cascade reactions.

Authors:  K C Nicolaou; Troy Lister; Ross M Denton; Christine F Gelin
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Review 2.  Contiguous stereogenic quaternary carbons: a daunting challenge in natural products synthesis.

Authors:  Emily A Peterson; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-01       Impact factor: 11.205

3.  Synthesis of 1,3-Diynes via Cadiot-Chodkiewicz Coupling of Volatile, in Situ Generated Bromoalkynes.

Authors:  Phil C Knutson; Haleigh E Fredericks; Eric M Ferreira
Journal:  Org Lett       Date:  2018-10-17       Impact factor: 6.005

4.  Synthesis of the B-seco limonoid core scaffold.

Authors:  Hanna Bruss; Hannah Schuster; Rémi Martinez; Markus Kaiser; Andrey P Antonchick; Herbert Waldmann
Journal:  Beilstein J Org Chem       Date:  2014-01-16       Impact factor: 2.883

5.  On the existence of and mechanism for microwave-specific reaction rate enhancement.

Authors:  Gregory B Dudley; Ranko Richert; A E Stiegman
Journal:  Chem Sci       Date:  2015-01-16       Impact factor: 9.825

6.  Synthesis and biological activities of petrosiols B and D.

Authors:  Jialin Geng; Qidong Ren; Caizhu Chang; Xinni Xie; Jun Liu; Yuguo Du
Journal:  RSC Adv       Date:  2019-04-01       Impact factor: 3.361
  6 in total

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