Literature DB >> 22827604

Spirastrellolide B: construction of the C(26)-C(40) northern hemisphere and a related [5,5,7]-bis-spiroketal analogue.

Xiaozhao Wang1, Thomas J Paxton, Ningkun Li, Amos B Smith.   

Abstract

Differential synthetic access to an advanced C26-C40 northern hemisphere fragment of spirastrellolide B and to a related [5,5,7]-bis-spiroketal analogue from a common intermediate has been achieved. Central to this venture is the regiocontrolled functionalization of a C(31-32) alkyne, exploiting different transition metal catalysts (cf. Pt(II) and Au(I)).

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Year:  2012        PMID： 22827604      PMCID： PMC3415318          DOI： 10.1021/ol301795a

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


  29 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.  Toward the synthesis of spirastrellolide A: construction of two C1-C25 diastereomers containing the BC-spiroacetal.

Authors:  Ian Paterson; Edward A Anderson; Stephen M Dalby; Olivier Loiseleur
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

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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  6 in total

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

Authors:  Alexander Sokolsky; Xiaozhao Wang; Amos B Smith
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

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.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

4.  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

5.  Total Synthesis of (-)-Secu'amamine A Exploiting Type II Anion Relay Chemistry.

Authors:  Heeoon Han; Amos B Smith
Journal:  Org Lett       Date:  2015-08-20       Impact factor: 6.005

6.  A mild, diastereoselective construction of cyclic and spirocyclic ketals employing a tandem photoisomerization/cyclization tactic.

Authors:  Bo Li; Brett D Williams; Amos B Smith
Journal:  Org Lett       Date:  2014-12-09       Impact factor: 6.005
  6 in total

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