Literature DB >> 16671802

New protocols for the assembly of the tetracyclic framework associated with the aromatic erythrina alkaloids.

Pauline C Stanislawski1, Anthony C Willis, Martin G Banwell.   

Abstract

[reaction: see text] Treatment of the anion derived from the ring-fused gem-dichlorocyclopropane 4c with silver tetrafluoroborate afforded the spirocyclic compound 17 in 74% yield. Product 17 was readily converted, over three steps, into the beta-iodoethyl derivative 20 and treatment of this latter compound with n-Bu(3)SnH then afforded, in 93% yield and via a radical addition/elimination sequence, compound 2 incorporating the ABCD framework of the aromatic erythrina alkaloids.

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Year:  2006        PMID: 16671802     DOI: 10.1021/ol060642c

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


  3 in total

1.  A [4 + 4] annulation strategy for the synthesis of eight-membered carbocycles based on intramolecular cycloadditions of conjugated enynes.

Authors:  Julia M Robinson; Sami F Tlais; Jennie Fong; Rick L Danheiser
Journal:  Tetrahedron       Date:  2011-12       Impact factor: 2.457

2.  Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans.

Authors:  Albert Padwa; Qiu Wang
Journal:  J Org Chem       Date:  2006-09-15       Impact factor: 4.354

3.  Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids.

Authors:  Nirav Kapadia; Wayne Harding
Journal:  Tetrahedron       Date:  2013-10-21       Impact factor: 2.457

  3 in total

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