Literature DB >> 26097261

Spirastrellolide E: Synthesis of an advanced C(1)-C(24) southern hemisphere.

Alexander Sokolsky1, Xiaozhao Wang1, Amos B Smith1.   

Abstract

The synthesis of a C(1)-C(24) advanced southern hemisphere fragment towards the total synthesis of spirastrellolide E has been achieved. Highlights of the route include a highly convergent Type I Anion Relay Chemistry (ARC) tactic for fragment assembly, in conjunction with a directed, regioselective gold-catalyzed alkyne functionalization to generate the central unsaturated [6,6]-spiroketal.

Entities:  

Keywords:  Anion Relay Chemistry; Brook Rearrangement; Gold Catalysis; Spirastrellolide; Total Synthesis

Year:  2015        PMID： 26097261      PMCID： PMC4470430          DOI： 10.1016/j.tetlet.2014.12.026

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  33 in total

1.  Synthesis of the C11-C23 fragment of spirastrellolide A. A ketal-tethered RCM approach to the construction of spiroketals.

Authors:  Jia Liu; Richard P Hsung
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

2.  Toward the total synthesis of spirastrellolide A. Part 1: Strategic considerations and preparation of the southern domain.

Authors:  Alois Fürstner; Michaël D B Fenster; Bernhard Fasching; Cédrickx Godbout; Karin Radkowski
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-18       Impact factor: 15.336

3.  Spirastrellolide B reveals the absolute configuration of the spirastrellolide macrolide core.

Authors:  Kaoru Warabi; David E Williams; Brian O Patrick; Michel Roberge; Raymond J Andersen
Journal:  J Am Chem Soc       Date:  2007-01-24       Impact factor: 15.419

4.  Synthesis of the DEF-bis-spiroacetal of spirastrellolide A exploiting a double asymmetric dihydroxylation/spiroacetalisation strategy.

Authors:  Ian Paterson; Edward A Anderson; Stephen M Dalby; Jong Ho Lim; Philip Maltas; Christian Moessner
Journal:  Chem Commun (Camb)       Date:  2006-09-20       Impact factor: 6.222

5.  Toward the total synthesis of spirastrellolide A. Part 3: intelligence gathering and preparation of a ring-expanded analogue.

Authors:  Alois Fürstner; Bernhard Fasching; Gregory W O'Neil; Michaël D B Fenster; Cédrickx Godbout; Julien Ceccon
Journal:  Chem Commun (Camb)       Date:  2007-06-26       Impact factor: 6.222

6.  Synthesis of two diastereomeric C1-C22 fragments of spirastrellolide A.

Authors:  Ian Paterson; Edward A Anderson; Stephen M Dalby; Julien Genovino; Jong Ho Lim; Christian Moessner
Journal:  Chem Commun (Camb)       Date:  2007-02-14       Impact factor: 6.222

7.  The stereocontrolled total synthesis of spirastrellolide A methyl ester. Expedient construction of the key fragments.

Authors:  Ian Paterson; Edward A Anderson; Stephen M Dalby; Jong Ho Lim; Philip Maltas; Olivier Loiseleur; Julien Genovino; Christian Moessner
Journal:  Org Biomol Chem       Date:  2012-04-16       Impact factor: 3.876

8.  Synthesis of the bis-spiroacetal core of the antimitotic agent spirastrellolide B.

Authors:  Jack Li-Yang Chen; Margaret A Brimble
Journal:  J Org Chem       Date:  2011-10-20       Impact factor: 4.354

9.  Spirastrellolide A, an antimitotic macrolide isolated from the Caribbean marine sponge Spirastrella coccinea.

Authors:  David E Williams; Michel Roberge; Rob Van Soest; Raymond J Andersen
Journal:  J Am Chem Soc       Date:  2003-05-07       Impact factor: 15.419

10.  Synthesis of the C1-C23 fragment of Spirastrellolide A.

Authors:  Jin-Haek Yang; Jia Liu; Richard P Hsung
Journal:  Org Lett       Date:  2008-05-17       Impact factor: 6.005
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  3 in total

1.  Type II Anion Relay Chemistry: Conformational Constraints To Achieve Effective [1,5]-Vinyl Brook Rearrangements.

Authors:  Qi Liu; Yu Chen; Xiao Zhang; K N Houk; Yong Liang; Amos B Smith
Journal:  J Am Chem Soc       Date:  2017-06-14       Impact factor: 15.419

2.  Synthesis of a C(1)-C(23) fragment for spirastrellolide E: development of a mechanistic rationale for spiroketalization.

Authors:  Alexander Sokolsky; Martin Cattoen; Amos B Smith
Journal:  Org Lett       Date:  2015-04-06       Impact factor: 6.005

3.  Synthesis of the C9-C25 Subunit of Spirastrellolide B.

Authors:  Soma Maitra; Mahipal Bodugam; Salim Javed; Paul R Hanson
Journal:  Org Lett       Date:  2016-06-14       Impact factor: 6.005
  3 in total

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