Literature DB >> 11312970

C-glycosides to fused polycyclic ethers. A formal synthesis of (+/-)-hemibrevetoxin B.

J D Rainier1, S P Allwein, J M Cox.   

Abstract

This paper describes a formal total synthesis of the marine ladder toxin hemibrevetoxin B from Danishefsky's dienes. This approach couples the generation of C-glycosides from cyclic enol ethers with metathesis or acid-mediated annulation reactions. The result is a highly efficient synthesis of the tetracyclic ring system of hemibrevetoxin B.

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Year:  2001        PMID： 11312970     DOI： 10.1021/jo001514j

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  16 in total

1.  Enol ethers as substrates for efficient Z- and enantioselective ring-opening/cross-metathesis reactions promoted by stereogenic-at-Mo complexes: utility in chemical synthesis and mechanistic attributes.

Authors:  Miao Yu; Ismail Ibrahem; Masayuki Hasegawa; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-24       Impact factor: 15.419

2.  Harnessing glycal-epoxide rearrangements: the generation of the AB, EF, and IJ rings of adriatoxin.

Authors:  Clement Osei Akoto; Jon D Rainier
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 3.  The continuing saga of the marine polyether biotoxins.

Authors:  K C Nicolaou; Michael O Frederick; Robert J Aversa
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  A highly convergent approach toward (-)-brevenal.

Authors:  Michael T Crimmins; Mariam Shamszad; Anita E Mattson
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

5.  Maitotoxin: An Inspiration for Synthesis.

Authors:  K C Nicolaou; Robert J Aversa
Journal:  Isr J Chem       Date:  2011-04       Impact factor: 3.333

6.  Synthesis of the WXYZA' domain of maitotoxin.

Authors:  K C Nicolaou; Thomas M Baker; Tsuyoshi Nakamura
Journal:  J Am Chem Soc       Date:  2010-12-17       Impact factor: 15.419

7.  Lewis Acid Catalyzed Carbonyl-Olefin Metathesis.

Authors:  Jacob R Ludwig; Corinna S Schindler
Journal:  Synlett       Date:  2017       Impact factor: 2.454

8.  Total synthesis of brevenal.

Authors:  Yuan Zhang; John Rohanna; Jie Zhou; Karthik Iyer; Jon D Rainier
Journal:  J Am Chem Soc       Date:  2011-02-15       Impact factor: 15.419

9.  Olefinic-lactone cyclizations to macrocycles.

Authors:  John C Rohanna; Jon D Rainier
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

10.  Olefinic ester and diene ring-closing metathesis using a reduced titanium alkylidene.

Authors:  Karthik Iyer; Jon D Rainier
Journal:  J Am Chem Soc       Date:  2007-09-27       Impact factor: 15.419
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