A macrolactonisation approach to the cembrane carbocycle of bielschowskysin

By judicious choice of a conformationally constraining unit to predispose cyclisation to a 15-membered ring, we present a straightforward strategy to a cembranolide precursor of bielschowskysin by the Sonogashira coupling of two readily prepared fragments (from d-glucose and l-malic acid) followed b...

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Bibliographic Details
Published inTetrahedron letters Vol. 54; no. 33; pp. 4406 - 4408
Main Authors Yang, Eugene G., Sekar, Karthik, Lear, Martin J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.08.2013
Elsevier
Subjects
Acylketene
Bielschowskysin
Chemistry
Chemistry, Organic
Constraining
Fragments
Furanocembranoid
Joining
Macrocyclisation
Physical Sciences
Precursors
Science & Technology
Sonogashira
Strategy
Tetrahedrons
Acylketene
Sonogashira
Macrocyclisation
Bielschowskysin
Furanocembranoid
CORE
ALCOHOLS
2+2 PHOTOCYCLOADDITION
AQUEOUS-MEDIA
BETA-KETO-ESTERS
STEREOSELECTIVE-SYNTHESIS
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Summary:By judicious choice of a conformationally constraining unit to predispose cyclisation to a 15-membered ring, we present a straightforward strategy to a cembranolide precursor of bielschowskysin by the Sonogashira coupling of two readily prepared fragments (from d-glucose and l-malic acid) followed by a facile β-acylketene macrolactonisation reaction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.06.012