Literature DB >> 18355075

Total synthesis of the marine metabolite (-)-clavosolide D.

Peter T Seden1, Jonathan P H Charmant, Christine L Willis.   

Abstract

The first total synthesis of the marine natural product (-)-clavosolide D is described confirming the structure of the unsymmetrical 16-membered diolide glycosylated by permethylated d-xylose moieties. Following efficient assembly of the two tetrahydropyrans using stereoselective Prins cyclizations, the side chains were introduced via an allylation/isomerization/anti cyclopropanation sequence; the final macrolactonization step was achieved under Yamaguchi conditions.

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Year:  2008        PMID： 18355075     DOI： 10.1021/ol800386d

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


  5 in total

1.  Mechanistic Analysis of Oxidative C-H Cleavages Using Inter- and Intramolecular Kinetic Isotope Effects.

Authors:  Hyung Hoon Jung; Paul E Floreancig
Journal:  Tetrahedron       Date:  2009-12-26       Impact factor: 2.457

2.  Cyanolide A, a glycosidic macrolide with potent Molluscicidal activity from the Papua New Guinea cyanobacterium Lyngbya bouillonii.

Authors:  Alban R Pereira; Christine F McCue; William H Gerwick
Journal:  J Nat Prod       Date:  2010-02-26       Impact factor: 4.050

3.  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

4.  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

5.  Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations.

Authors:  Ryan J Beattie; Thomas W Hornsby; Gemma Craig; M Carmen Galan; Christine L Willis
Journal:  Chem Sci       Date:  2016-01-11       Impact factor: 9.825
  5 in total

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