Total Synthesis of the Marine Metabolite (−)-Clavosolide D

Total Synthesis of the Marine Metabolite (−)-Clavosolide D

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,...

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Veröffentlicht in:Organic letters 2008-04, Vol.10 (8), p.1637-1640
Hauptverfasser: Seden, Peter T, Charmant, Jonathan P. H, Willis, Christine L
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Cyclization
Macrolides - chemical synthesis
Macrolides - chemistry
Marine Biology
Models, Molecular
Porifera
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol800386d