Literature DB >> 21456515

Tandem metathesis reactions of oxabicyclo[2.2.1]heptenes: studies on the spirocyclic core of cyclopamine.

E Zachary Oblak1, Narendran G-Dayanandan, Dennis L Wright.   

Abstract

A rapid approach to the spirocyclic core of cyclopamine was achieved in four steps from 2-pentenyl-furan. A furan Diels-Alder reaction followed by a one-pot dehalogenation/amination sequence provides the oxabicyclic triene that upon treatment with Grubbs' catalyst undergoes smooth rearrangement to the tricyclic core.

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Year:  2011        PMID: 21456515     DOI: 10.1021/ol200706f

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


  4 in total

1.  De Novo Synthesis of the DEF-Ring Stereotriad Core of the Veratrum Alkaloids.

Authors:  Matthew A Horwitz; Jacob G Robins; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2020-04-30       Impact factor: 4.354

2.  Progress toward a Convergent, Asymmetric Synthesis of Jervine.

Authors:  Blane P Zavesky; Pedro De Jesús Cruz; Jeffrey S Johnson
Journal:  Org Lett       Date:  2020-04-14       Impact factor: 6.005

3.  The tandem ring opening/ring closing metathesis route to oxaspirocycles: an approach to phelligridin G.

Authors:  Harold D Cooper; Dennis L Wright
Journal:  Molecules       Date:  2013-02-21       Impact factor: 4.411

4.  Enantioselective Total Synthesis of (+)-Heilonine.

Authors:  Kyle J Cassaidy; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2021-09-29       Impact factor: 15.419

  4 in total

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