Literature DB >> 16506747

Total synthesis of dolabelide D.

Peter K Park1, Steven J O'Malley, Darby R Schmidt, James L Leighton.   

Abstract

The first total synthesis of dolabelide D (or of any of the closely related dolabelides) has been achieved with a longest linear sequence of 17 steps. Key features of the synthesis include an application of the catalytic asymmetric silane alcoholysis, the tandem silylformylation-crotylsilylation, and a Brook-like 1,4-carbon to oxygen silyl migration.

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Year:  2006        PMID： 16506747      PMCID： PMC2529159          DOI： 10.1021/ja058692k

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 in total

1.  A highly practical and enantioselective reagent for the allylation of aldehydes.

Authors:  Katsumi Kubota; James L Leighton
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-24       Impact factor: 15.336

2.  Stereoselective synthesis of the C(1)-C(13) segment of dolabelide B.

Authors:  Gary E Keck; Mark D McLaws
Journal:  Tetrahedron Lett       Date:  2005-07-18       Impact factor: 2.415

3.  Diastereoselective synthesis of protected syn 1,3-diols: preparation of the C16-C24 portion of Dolabelides.

Authors:  Laurence Grimaud; Romain de Mesmay; Joëlle Prunet
Journal:  Org Lett       Date:  2002-02-07       Impact factor: 6.005

4.  Prevention of undesirable isomerization during olefin metathesis.

Authors:  Soon Hyeok Hong; Daniel P Sanders; Choon Woo Lee; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

5.  A practical synthesis of (+)-discodermolide and analogues: fragment union by complex aldol reactions.

Authors:  I Paterson; G J Florence; K Gerlach; J P Scott; N Sereinig
Journal:  J Am Chem Soc       Date:  2001-10-03       Impact factor: 15.419

6.  Copper(I) tert-butoxide-promoted 1,4 C(sp(2))-to-O silyl migration: stereospecific allylation of (Z)-gamma-trimethylsilyl allylic alcohols.

Authors:  H Taguchi; K Ghoroku; M Tadaki; A Tsubouchi; T Takeda
Journal:  Org Lett       Date:  2001-11-15       Impact factor: 6.005

7.  Approach to the synthesis of dolabelides A and B: fragment synthesis by tandem silylformylation-crotylsilylation.

Authors:  Darby R Schmidt; Peter K Park; James L Leighton
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

8.  Tandem intramolecular silylformylation-crotylsilylation: highly efficient synthesis of polyketide fragments.

Authors:  Michael J Zacuto; Steven J O'Malley; James L Leighton
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

9.  Catalytic asymmetric silane alcoholysis: practical access to chiral silanes.

Authors:  Darby R Schmidt; Steven J O'Malley; James L Leighton
Journal:  J Am Chem Soc       Date:  2003-02-05       Impact factor: 15.419

10.  Synthesis of the antifungal macrolide antibiotic (+)-roxaticin.

Authors:  David A Evans; Brian T Connell
Journal:  J Am Chem Soc       Date:  2003-09-10       Impact factor: 15.419
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  17 in total

1.  Super silyl stereo-directing groups for complete 1,5-syn and -anti stereoselectivities in the aldol reactions of beta-siloxy methyl ketones with aldehydes.

Authors:  Yousuke Yamaoka; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

Review 2.  Marine Mollusk-Derived Agents with Antiproliferative Activity as Promising Anticancer Agents to Overcome Chemotherapy Resistance.

Authors:  Maria Letizia Ciavatta; Florence Lefranc; Marianna Carbone; Ernesto Mollo; Margherita Gavagnin; Tania Betancourt; Ramesh Dasari; Alexander Kornienko; Robert Kiss
Journal:  Med Res Rev       Date:  2016-12-07       Impact factor: 12.944

Review 3.  Bioactive Compounds from Marine Heterobranchs.

Authors:  Conxita Avila; Carlos Angulo-Preckler
Journal:  Mar Drugs       Date:  2020-12-21       Impact factor: 5.118

4.  Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling.

Authors:  Julie L Hofstra; Alan H Cherney; Ciara M Ordner; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2017-12-20       Impact factor: 15.419

5.  A multifaceted phosphate tether: application to the C1-C14 subunit of dolabelides A-D.

Authors:  Joshua D Waetzig; Paul R Hanson
Journal:  Org Lett       Date:  2007-12-07       Impact factor: 6.005

6.  Total syntheses of (+/-)-platencin and (-)-platencin.

Authors:  K C Nicolaou; G Scott Tria; David J Edmonds; Moumita Kar
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

7.  Si-based benzylic 1,4-rearrangement/cyclization reaction.

Authors:  Barry M Trost; Andreas Bertogg
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

8.  Divalent and Multivalent Activation in Phosphate Triesters: A Versatile Method for the Synthesis of Advanced Polyol Synthons.

Authors:  Christopher D Thomas; James P McParland; Paul R Hanson
Journal:  European J Org Chem       Date:  2009-10-08

9.  Molybdenum-based complexes with two aryloxides and a pentafluoroimido ligand: catalysts for efficient Z-selective synthesis of a macrocyclic trisubstituted alkene by ring-closing metathesis.

Authors:  Chenbo Wang; Fredrik Haeffner; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-10       Impact factor: 15.336

10.  A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D.

Authors:  Alan Whitehead; Joshua D Waetzig; Christopher D Thomas; Paul R Hanson
Journal:  Org Lett       Date:  2008-03-07       Impact factor: 6.005
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