Literature DB >> 22116256

Tandem Payne/Meinwald versus Meinwald rearrangements on the α-hydroxy- or α-silyloxy-spiro epoxide skeleton.

Jane Totobenazara1, Heloua Haroun, Julien Rémond, Karim Adil, Fabrice Dénès, Jacques Lebreton, Catherine Gaulon-Nourry, Pascal Gosselin.   

Abstract

Under Lewis acid activation, the new α-hydroxy-spiro epoxide scaffold 1a underwent an original tandem Payne/Meinwald rearrangement affording the cyclopentyl hydroxymethylketone 6 in a stereospecific manner, while a Meinwald-type epoxide rearrangement occurred when the derived α-trimethylsilyloxy-spiro epoxide 2a was treated with MABR, yielding stereoselectively the cyclohexane carbaldehyde 9.

Entities:  

Year:  2011        PMID： 22116256     DOI： 10.1039/c1ob06776a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  2 in total

1.  Development of a Unified Enantioselective, Convergent Synthetic Approach Toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Asymmetric Formation of the Polycyclic Norditerpenoid Carbocyclic Core by Tandem Annulation Cascade.

Authors:  Robert A Craig; Russell C Smith; Jennifer L Roizen; Amanda C Jones; Scott C Virgil; Brian M Stoltz
Journal:  J Org Chem       Date:  2018-03-19       Impact factor: 4.354

2.  Secondary Organic Aerosol Formation via 2-Methyl-3-buten-2-ol Photooxidation: Evidence of Acid-Catalyzed Reactive Uptake of Epoxides.

Authors:  Haofei Zhang; Zhenfa Zhang; Tianqu Cui; Ying-Hsuan Lin; Neil A Bhathela; John Ortega; David R Worton; Allen H Goldstein; Alex Guenther; Jose L Jimenez; Avram Gold; Jason D Surratt
Journal:  Environ Sci Technol Lett       Date:  2014-03-18
  2 in total

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