Literature DB >> 16468736

Total synthesis, structural revision, and absolute configuration of (-)-clavosolide [corrected] A.

Jung Beom Son1, Si Nae Kim, Na Yeong Kim, Duck Hyung Lee.   

Abstract

[reaction: see text] Enantioselective synthesis of 3, a revised structure for clavosolide A, was completed. Both (1)H and (13)C NMR spectra of the natural and synthetic compounds were identical, and optical rotation measurements identified the absolute configuration of the natural clavosolide A as [corrected] 3.

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Year:  2006        PMID： 16468736     DOI： 10.1021/ol052851n

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


  13 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.  Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

Authors:  Takashi L Suyama; William H Gerwick; Kerry L McPhail
Journal:  Bioorg Med Chem       Date:  2011-06-12       Impact factor: 3.641

3.  Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.

Authors:  James M Cabrera; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-24       Impact factor: 15.336

4.  Cyclopropane compatibility with oxidative carbocation formation: total synthesis of clavosolide A.

Authors:  GuangRong Peh; Paul E Floreancig
Journal:  Org Lett       Date:  2012-10-24       Impact factor: 6.005

5.  Total synthesis of cyanolide A in the absence of protecting groups, chiral auxiliaries, or premetalated carbon nucleophiles.

Authors:  Andrew R Waldeck; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-11       Impact factor: 15.336

6.  Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria.

Authors:  Sarath P Gunasekera; Yang Li; Ranjala Ratnayake; Danmeng Luo; Jeannette Lo; Joseph H Reibenspies; Zhengshuang Xu; Michael J Clare-Salzler; Tao Ye; Valerie J Paul; Hendrik Luesch
Journal:  Chemistry       Date:  2016-05-03       Impact factor: 5.236

7.  Symmetric macrocycles by a Prins dimerization and macrocyclization strategy.

Authors:  Michael R Gesinski; Kwanruthai Tadpetch; Scott D Rychnovsky
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

Review 8.  Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Authors:  Anne-Marie R Dechert-Schmitt; Daniel C Schmitt; Xin Gao; Takahiko Itoh; Michael J Krische
Journal:  Nat Prod Rep       Date:  2014-02-11       Impact factor: 13.423

9.  Total Synthesis of Clavosolide A via Tandem Allylic Oxidation/Oxa-Conjugate Addition Reaction.

Authors:  Joseph B Baker; Hyoungsu Kim; Jiyong Hong
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

10.  Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors:  Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-26       Impact factor: 15.419
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