Literature DB >> 15787498

Expedient construction of the vibsanin E core without the use of protecting groups.

Ralf Heim1, Stefan Wiedemann, Craig M Williams, Paul V Bernhardt.   

Abstract

[reaction: see text] The tricyclic core of vibsanin E was constructed without the use of a protecting group in six steps. The El Gaïed Baylis-Hillman variant was key to allowing the Brønsted acid induced tandem cyclization forming rings B and C in one operation.

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Year:  2005        PMID： 15787498     DOI： 10.1021/ol0501222

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


  6 in total

1.  Towards the Total Synthesis of 3-Hydroxyvibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Paul V Bernhardt; Huw M L Davies; Craig M Williams
Journal:  Synthesis (Stuttg)       Date:  2009-09-01       Impact factor: 3.157

2.  A mechanistic investigation into the zinc carbenoid-mediated homologation reaction by DFT methods: is a classical donor-acceptor cyclopropane intermediate involved?

Authors:  Wilhelm A Eger; Charles K Zercher; Craig M Williams
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

3.  A combined DFT and NMR investigation of the zinc organometallic intermediate proposed in the syn-selective tandem chain extension-aldol reaction of β-keto esters.

Authors:  Karelle S Aiken; Wilhelm A Eger; Craig M Williams; Carley M Spencer; Charles K Zercher
Journal:  J Org Chem       Date:  2012-07-03       Impact factor: 4.354

4.  Total Synthesis of (±)-Vibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Huw M L Davies; Craig M Williams
Journal:  Aust J Chem       Date:  2009       Impact factor: 1.321

5.  Asymmetric [4 + 3] cycloadditions between vinylcarbenoids and dienes: application to the total synthesis of the natural product (-)-5-epi-vibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Yajing Lian; Huw M L Davies; Craig M Williams
Journal:  J Am Chem Soc       Date:  2009-06-17       Impact factor: 15.419

6.  End game strategies towards the total synthesis of vibsanin E, 3-hydroxyvibsanin E, furanovibsanin A, and 3-O-methylfuranovibsanin A.

Authors:  Brett D Schwartz; Craig M Williams; Paul V Bernhardt
Journal:  Beilstein J Org Chem       Date:  2008-10-08       Impact factor: 2.883
  6 in total

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