Literature DB >> 15816757

Synthesis of the putative structure of tridachiahydropyrone.

David W Jeffery1, Michael V Perkins, Jonathan M White.   

Abstract

[reaction: see text] A short total synthesis of the putative structure of the marine natural product tridachiahydropyrone as a single enantiomer is described. Novel steps include a cuprate addition and cyclization to form a cyclohexanone ring and formation of the bicyclic pyrone with P(2)O(5) on Celite. The spectroscopic data obtained for compound 1 do not match those reported for tridachiahydropyrone; therefore, revision of the assigned natural product structure is warranted.

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Year:  2005        PMID: 15816757     DOI: 10.1021/ol050236d

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


  2 in total

Review 1.  Recent synthetic studies leading to structural revisions of marine natural products.

Authors:  Yoshihide Usami
Journal:  Mar Drugs       Date:  2009-07-13       Impact factor: 5.118

2.  Total synthesis of auripyrone A using a tandem non-aldol aldol/Paterson aldol process as a key step.

Authors:  Michael E Jung; Ramin Salehi-Rad
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

  2 in total

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