Literature DB >> 16494495

A hetero-Diels-Alder approach to complex pyrones: an improved synthesis of the spongistatin AB spiroketal.

Michael T Crimmins1, Aaron C Smith.   

Abstract

The conversion of a substituted dioxinone to a pyrone was used in an improved synthesis of the AB spiroketal subunit of the spongistatins. This transformation occurred via a hetero-Diels-Alder reaction of an acyl ketene with butyl vinyl ether. A double diastereoselective Mukaiyama aldol reaction is used to provide the hetero-Diels-Alder precursor.

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Year:  2006        PMID： 16494495      PMCID： PMC2546580          DOI： 10.1021/ol0601601

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


  9 in total

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Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

2.  The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride. The merged stereochemical impact of alpha- and beta-stereocenters in chelate-controlled carbonyl addition reactions with enolsilane and hydride nucleophiles.

Authors:  D A Evans; B D Allison; M G Yang; C E Masse
Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

3.  An aldol approach to the synthesis of the EF fragment of spongistatin 1.

Authors:  M T Crimmins; J D Katz; L C McAtee; E A Tabet; S J Kirincich
Journal:  Org Lett       Date:  2001-03-22       Impact factor: 6.005

4.  Asymmetric total synthesis of spongistatins 1 and 2.

Authors:  Michael T Crimmins; Jason D Katz; David G Washburn; Shawn P Allwein; Laura F McAtee
Journal:  J Am Chem Soc       Date:  2002-05-22       Impact factor: 15.419

5.  Synthesis of the C16-C28 spiroketal subunit of spongistatin 1 (altohyrtin A): the pyrone approach.

Authors:  M T Crimmins; J D Katz
Journal:  Org Lett       Date:  2000-04-06       Impact factor: 6.005

6.  Spongistatin synthetic studies. evolution of a scalable synthesis for the EF fragment of (+)-Spongistatin 1 exploiting a Petasis-Ferrier union/rearrangement tactic.

Authors:  Amos B Smith; Chris Sfouggatakis; Dimitar B Gotchev; Shohei Shirakami; David Bauer; Wenyu Zhu; Victoria A Doughty
Journal:  Org Lett       Date:  2004-09-30       Impact factor: 6.005

7.  Spongistatin 1, a highly cytotoxic, sponge-derived, marine natural product that inhibits mitosis, microtubule assembly, and the binding of vinblastine to tubulin.

Authors:  R Bai; Z A Cichacz; C L Herald; G R Pettit; E Hamel
Journal:  Mol Pharmacol       Date:  1993-10       Impact factor: 4.436

8.  TADDOLs, Their Derivatives, and TADDOL Analogues: Versatile Chiral Auxiliaries.

Authors:  Dieter Seebach; Albert K. Beck; Alexander Heckel
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

9.  The spongistatins, potently cytotoxic inhibitors of tubulin polymerization, bind in a distinct region of the vinca domain.

Authors:  R Bai; G F Taylor; Z A Cichacz; C L Herald; J A Kepler; G R Pettit; E Hamel
Journal:  Biochemistry       Date:  1995-08-01       Impact factor: 3.162
  9 in total
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Review 2.  Bond formations by intermolecular and intramolecular trappings of acylketenes and their applications in natural product synthesis.

Authors:  Keith P Reber; S David Tilley; Erik J Sorensen
Journal:  Chem Soc Rev       Date:  2009-09-02       Impact factor: 54.564

3.  Iridium-catalyzed regio- and enantioselective allylic substitution of silyl dienolates derived from dioxinones.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-15       Impact factor: 15.336
  3 in total

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