Literature DB >> 17266323

A short, formal, biomimetic synthesis of (+/-)-polygalolides A and B.

Barry B Snider1, Xiaoxing Wu, Seiichi Nakamura, Shunichi Hashimoto.   

Abstract

[reaction: see text] Reaction of bisacetoxy pyranone 9 with Et3N gave 3-oxidopyrylium ylide 10, which underwent a stereo- and regiospecific [5 + 2] cycloaddition with alpha-methylenebutyrolactone to afford 16 (34%). Treatment of 16 with Cs2CO3 resulted in hydrolysis of the lactone and acetate and conjugate addition of the hydroxyethyl group to the enone. Lactonization on acidification afforded 4 (57%), completing a two-step, formal synthesis of polygalolides A and B.

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Year:  2007        PMID： 17266323      PMCID： PMC2532947          DOI： 10.1021/ol0630898

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


  2 in total

1.  New phenolics from Polygala fallax.

Authors:  Wenzhe Ma; Xiaoyi Wei; Tiejun Ling; Haihui Xie; Wenhua Zhou
Journal:  J Nat Prod       Date:  2003-03       Impact factor: 4.050

2.  Total synthesis and absolute stereochemistry of polygalolides A and B.

Authors:  Seiichi Nakamura; Yukihito Sugano; Fumiaki Kikuchi; Shunichi Hashimoto
Journal:  Angew Chem Int Ed Engl       Date:  2006-10-06       Impact factor: 15.336
  2 in total
  4 in total

1.  Maltol- and Allomaltol-Derived Oxidopyrylium Ylides: Methyl Substitution Pattern Kinetically Influences [5 + 3] Dimerization versus [5 + 2] Cycloaddition Reactions.

Authors:  Lauren P Bejcek; Aswin K Garimallaprabhakaran; Duygu M Suyabatmaz; Alexander Greer; William H Hersh; Edyta M Greer; Ryan P Murelli
Journal:  J Org Chem       Date:  2019-10-25       Impact factor: 4.354

2.  Oxidopyrylium [5+2] Cycloaddition Chemistry: Historical Perspective and Recent Advances (2008-2018).

Authors:  Lauren P Bejcek; Ryan P Murelli
Journal:  Tetrahedron       Date:  2018-04-05       Impact factor: 2.457

3.  Investigations into a Stoichiometrically Equivalent Intermolecular Oxidopyrylium [5 + 2] Cycloaddition Reaction Leveraging 3-Hydroxy-4-pyrone-Based Oxidopyrylium Dimers.

Authors:  Daniel V Schiavone; Diana M Kapkayeva; Ryan P Murelli
Journal:  J Org Chem       Date:  2021-02-15       Impact factor: 4.354

4.  Synthesis of the C9-C25 Subunit of Spirastrellolide B.

Authors:  Soma Maitra; Mahipal Bodugam; Salim Javed; Paul R Hanson
Journal:  Org Lett       Date:  2016-06-14       Impact factor: 6.005
  4 in total

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