Literature DB >> 17061881

The total synthesis of (+)-tedanolide.

Gunnar Ehrlich1, Jorma Hassfeld, Ulrike Eggert, Markus Kalesse.   

Abstract

The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations generate the macrocyclic triketone. In the endgame of the synthesis, four TBS groups are removed in one reaction and a chemo- and stereoselective final step epoxidation generates (+)-tedanolide.

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Year:  2006        PMID: 17061881     DOI: 10.1021/ja0659572

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  Stereochemically versatile synthesis of the C1-C12 fragment of tedanolide C.

Authors:  Thomas E Smith; Sarah J Fink; Zebulon G Levine; Kerani A McClelland; Adrian A Zackheim; Mary E Daub
Journal:  Org Lett       Date:  2012-02-29       Impact factor: 6.005

2.  anti-Diastereo- and enantioselective carbonyl (hydroxymethyl)allylation from the alcohol or aldehyde oxidation level: allyl carbonates as allylmetal surrogates.

Authors:  Yong Jian Zhang; Jin Haek Yang; Sang Hoon Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2010-04-07       Impact factor: 15.419

3.  Total syntheses of (+)-tedanolide and (+)-13-deoxytedanolide.

Authors:  Joshua R Dunetz; Lisa D Julian; Jason S Newcom; William R Roush
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

4.  Candidaspongiolides, distinctive analogues of tedanolide from sponges of the genus Candidaspongia.

Authors:  Tamara L Meragelman; Richard H Willis; Girma M Woldemichael; Andrew Heaton; Peter T Murphy; Kenneth M Snader; David J Newman; Rob van Soest; Michael R Boyd; John H Cardellina; Tawnya C McKee
Journal:  J Nat Prod       Date:  2007-06-12       Impact factor: 4.050

5.  Two new cytotoxic candidaspongiolides from an indonesian sponge.

Authors:  Agus Trianto; Idam Hermawan; Toshimasa Suzuka; Junichi Tanaka
Journal:  ISRN Pharm       Date:  2011-07-18

6.  Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment.

Authors:  Jan Geldsetzer; Markus Kalesse
Journal:  Beilstein J Org Chem       Date:  2020-04-14       Impact factor: 2.883

Review 7.  Macrocyclic drugs and synthetic methodologies toward macrocycles.

Authors:  Xufen Yu; Dianqing Sun
Journal:  Molecules       Date:  2013-05-24       Impact factor: 4.411

  7 in total

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