Literature DB >> 12517144

Total synthesis of (+)-13-deoxytedanolide.

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

Abstract

In this communication we describe the first total synthesis of (+)-13-deoxytedanolide, an architecturally complex marine macrolide possessing significant antitumor activity. The cornerstone of the synthesis comprises a highly convergent dithiane coupling used to construct the carbon skeleton, followed by a novel use of the Evans-Tishchenko reduction to oxidize the C(1) aldehyde to an ester in the presence of the oxidatively labile dithiane.

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Year:  2003        PMID: 12517144     DOI: 10.1021/ja0289649

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


  9 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.  Novel approach to multifunctionalized homoallylic alcohols via regioselective ring opening of aryl oxiranes with 3-iodo allenoates.

Authors:  Adiseshu Kattuboina; Parminder Kaur; Cody Timmons; Guigen Li
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

3.  Myriaporone 3/4 structure--activity relationship studies define a pharmacophore targeting eukaryotic protein synthesis.

Authors:  John Hines; Myriam Roy; Hua Cheng; Christina M Agapakis; Richard Taylor; Craig M Crews
Journal:  Mol Biosyst       Date:  2006-05-26

4.  18O assisted analysis of a γ,δ-epoxyketone cyclization: synthesis of the C16-C28 fragment of ammocidin D.

Authors:  Stephen T Chau; Yoichi Hayakawa; Gary A Sulikowski
Journal:  Org Lett       Date:  2011-01-19       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.  Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers.

Authors:  Jacqueline D Hicks; Chan Woo Huh; Ashley D Legg; William R Roush
Journal:  Org Lett       Date:  2007-11-21       Impact factor: 6.005

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

Authors:  Amos B Smith; Christopher M Adams; Stephanie A Lodise Barbosa; Andrew P Degnan
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-26       Impact factor: 11.205

Review 8.  Synthetic efforts on the road to marine natural products bearing 4-O-2,3,4,6-tetrasubstituted THPs: an update.

Authors:  Marta Fariña-Ramos; Celina García; Víctor S Martín; Sergio J Álvarez-Méndez
Journal:  RSC Adv       Date:  2021-02-03       Impact factor: 3.361

9.  Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation.

Authors:  Mrunesh Koli; Sucheta Chatterjee; Subrata Chattopadhyay; Dibakar Goswami
Journal:  Beilstein J Org Chem       Date:  2018-08-22       Impact factor: 2.883

  9 in total

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