Literature DB >> 16494470

Progress toward the total synthesis of Bielschowskysin: a stereoselective [2+2] photocycloaddition.

Brandon Doroh1, Gary A Sulikowski.   

Abstract

The tetracyclic core of the diterpene bielschowskysin has been prepared as a single enantiomer via a stereoselective intramolecular [2+2] photocycloaddition of 5-alkylidene-2(5H)-furanone 3.

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Year:  2006        PMID： 16494470      PMCID： PMC2527052          DOI： 10.1021/ol0530225

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


  3 in total

1.  Isolation and structure of providencin: a highly oxygenated diterpene possessing a unique bicyclo[12.2.0]hexadecane ring system from the sea plume Pseudopterogorgia kallos.

Authors:  Jeffrey Marrero; Abimael D Rodríguez; Peter Baran; Raphael G Raptis
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

2.  Bielschowskysin, a gorgonian-derived biologically active diterpene with an unprecedented carbon skeleton.

Authors:  Jeffrey Marrero; Abimael D Rodríguez; Peter Baran; Raphael G Raptis; Juan A Sánchez; Eduardo Ortega-Barria; Todd L Capson
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005

3.  Isolation and characterization of kallosin A, a novel rearranged pseudopterane diterpenoid from the Caribbean sea plume Pseudopterogorgia kallos (Bielschowsky).

Authors:  Jeffrey Marrero; Abimael D Rodríguez; Peter Baran; Raphael G Raptis
Journal:  J Org Chem       Date:  2003-06-13       Impact factor: 4.354
  3 in total
  9 in total

1.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

2.  A strategy toward the synthesis of C13-oxidized cembrenolides.

Authors:  Alec Saitman; Steven D E Sullivan; Emmanuel A Theodorakis
Journal:  Tetrahedron Lett       Date:  2013-03-20       Impact factor: 2.415

3.  Synthesis of a highly functionalized core of verrillin.

Authors:  Alec Saitman; Emmanuel A Theodorakis
Journal:  Org Lett       Date:  2013-04-30       Impact factor: 6.005

Review 4.  Polycyclic Furanobutenolide-Derived Cembranoid and Norcembranoid Natural Products: Biosynthetic Connections and Synthetic Efforts.

Authors:  Robert A Craig; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-05-18       Impact factor: 60.622

5.  Synthesis of macroheterocycles through intramolecular oxidative coupling of furanoid β-ketoesters.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Ebner; Christian Nilewski; Christopher F Ahles; Derek Rhoades
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-05       Impact factor: 15.336

6.  An expedient synthesis of a functionalized core structure of bielschowskysin.

Authors:  K C Nicolaou; Vikrant A Adsool; Christopher R H Hale
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-26       Impact factor: 15.336

7.  Total Synthesis of Potent Antitumor Macrolide, (-)-Zampanolide: An Oxidative Intramolecular Cyclization-Based Strategy.

Authors:  Arun K Ghosh; Xu Cheng; Ruoli Bai; Ernest Hamel
Journal:  European J Org Chem       Date:  2012-07-01

8.  Use of a palladium(II)-catalyzed oxidative kinetic resolution in synthetic efforts toward bielschowskysin.

Authors:  Michael E Meyer; John H Phillips; Eric M Ferreira; Brian M Stoltz
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

9.  A palladium-catalyzed carbo-oxygenation: the bielschowskysin case.

Authors:  Martin Himmelbauer; Jean-Baptiste Farcet; Julien Gagnepain; Johann Mulzer
Journal:  Org Lett       Date:  2013-05-31       Impact factor: 6.005
  9 in total

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