Literature DB >> 19053739

Consecutive alkene cross-metathesis/oxonium ylide formation-rearrangement: synthesis of the anti-HIV agent hyperolactone C.

David M Hodgson1, Deepshikha Angrish, Stephanie P Erickson, Johannes Kloesges, Caroline H Lee.   

Abstract

Alpha-diazo-beta-ketoesters bearing allylic ether functionality undergo highly stereoselective Ru-carbene-catalyzed alkene cross-metathesis followed by Rh(2)(OAc)(4)-catalyzed oxonium ylide formation/[2,3] sigmatropic rearrangement in a one-flask operation and in a highly diastereoselective manner. The methodology has been demonstrated in a concise synthesis of the anti-HIV agent hyperolactone C.

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Year:  2008        PMID： 19053739     DOI： 10.1021/ol802334y

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


  4 in total

1.  Total synthesis and structural revision of biyouyanagin B.

Authors:  K C Nicolaou; Silvano Sanchini; T Robert Wu; David Sarlah
Journal:  Chemistry       Date:  2010-07-12       Impact factor: 5.236

Review 2.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

3.  Stereodivergent synthesis of vicinal quaternary-quaternary stereocenters and bioactive hyperolactones.

Authors:  Haifeng Zheng; Yan Wang; Chaoran Xu; Xi Xu; Lili Lin; Xiaohua Liu; Xiaoming Feng
Journal:  Nat Commun       Date:  2018-05-17       Impact factor: 14.919

4.  A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes.

Authors:  Karim A Bahou; D Christopher Braddock; Adam G Meyer; G Paul Savage; Zhensheng Shi; Tianyou He
Journal:  J Org Chem       Date:  2020-03-19       Impact factor: 4.354
  4 in total

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