Literature DB >> 15163795

A unified approach to the tedanolides: total synthesis of (+)-13-deoxytedanolide.

Amos B Smith1, Christopher M Adams, Stephanie A Lodise Barbosa, Andrew P Degnan.   

Abstract

A unified approach for the construction of the potent marine antitumor agents (+)-tedanolide (1) and (+)-13-deoxytedanolide (2) is described. Highlights of the synthetic strategy include the development of a versatile bifunctional dithiane-vinyl iodide linchpin, the unorthodox use of the Evans-Tishchenko reaction, and a late-stage high-risk stereocontrolled introduction of the C(18,19) epoxide to achieve a total synthesis of (+)-13-deoxytedanolide (2).

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Year:  2004        PMID： 15163795      PMCID： PMC514431          DOI： 10.1073/pnas.0402084101

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  13 in total

1.  Synthetic studies of an 18-membered antitumor macrolide, tedanolide. 6. Synthesis of a key intermediate via a highly efficient macrolactonization of computer-aid designed seco-acid.

Authors:  T Matsushima; N Nakajima; B Z Zheng; O Yonemitsu
Journal:  Chem Pharm Bull (Tokyo)       Date:  2000-06       Impact factor: 1.645

2.  Novel deprotection of SEM ethers: A very mild and selective method using magnesium bromide

Authors: 
Journal:  Org Lett       Date:  2000-05-18       Impact factor: 6.005

3.  Sequencing Reactions with Samarium(II) Iodide.

Authors:  Gary A. Molander; Christina R. Harris
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

4.  Synthesis of a fully functionalized protected C1-C11 fragment for the synthesis of the tedanolides.

Authors:  M E Jung; C P Lee
Journal:  Org Lett       Date:  2001-02-08       Impact factor: 6.005

5.  SmI(2)-promoted oxidation of aldehydes in the presence of electron-rich heteroatoms.

Authors:  Amos B Smith; Dongjoo Lee; Christopher M Adams; Marisa C Kozlowski
Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

6.  Total synthesis of (+)-13-deoxytedanolide.

Authors:  Amos B Smith; Christopher M Adams; Stephanie A Lodise Barbosa; Andrew P Degnan
Journal:  J Am Chem Soc       Date:  2003-01-15       Impact factor: 15.419

7.  Synthesis of tedanolide and 13-deoxytedanolide. Assembly of a common C(1)-C(11) subtarget.

Authors:  A B Smith; S A Lodise
Journal:  Org Lett       Date:  1999-10-21       Impact factor: 6.005

8.  Studies on the synthesis of tedanolide. 2. Stereoselective synthesis of a protected C(1)-C(12) fragment.

Authors:  William R Roush; Jason S Newcom
Journal:  Org Lett       Date:  2002-12-26       Impact factor: 6.005

9.  Halo sugar nucleosides. I. Iodination of the primary hydroxyl groups of nucleosides with methyltriphenoxyphosphonium iodide.

Authors:  J P Verheyden; J G Moffatt
Journal:  J Org Chem       Date:  1970-07       Impact factor: 4.354

10.  A divergent approach to the myriaporones and tedanolide: completion of the carbon skeleton of myriaporone 1.

Authors:  Richard E Taylor; Brian R Hearn; Jeffrey P Ciavarri
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005
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  6 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.  SYNTHESIS OF (S,S)-DIISOPROPYL TARTRATE (E)-CROTYLBORONATE AND ITS REACTION WITH ALDEHYDES: (2R,3R,4R)-1,2-DIDEOXY-2-ETHENYL-4,5-O-(1-METHYLETHYLIDENE)-XYLITOL.

Authors:  Huikai Sun; William R Roush; David A Candito; Mathieu Blanchot; Mark Lautens
Journal:  Organic Synth       Date:  2011

3.  Enantioselective hydroformylation of N-vinyl carboxamides, allyl carbamates, and allyl ethers using chiral diazaphospholane ligands.

Authors:  Richard I McDonald; Gene W Wong; Ram P Neupane; Shannon S Stahl; Clark R Landis
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

4.  Synthesis of caeliferins, elicitors of plant immune responses: accessing lipophilic natural products via cross metathesis.

Authors:  Inish O'Doherty; Joshua J Yim; Eric A Schmelz; Frank C Schroeder
Journal:  Org Lett       Date:  2011-10-12       Impact factor: 6.005

5.  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

6.  Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: a powerful entry into chiral building blocks.

Authors:  Barry M Trost; Sushant Malhotra; Takashi Mino; Naomi S Rajapaksa
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
  6 in total

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