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,...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 10; no. 8; pp. 1637 - 1640
Main Authors Seden, Peter T, Charmant, Jonathan P. H, Willis, Christine L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.04.2008
Amer Chemical Soc
Subjects
Animals
Chemistry
Chemistry, Organic
Cyclization
Macrolides - chemical synthesis
Macrolides - chemistry
Marine Biology
Models, Molecular
Physical Sciences
Porifera
Science & Technology
CLAVOSOLIDE-A
REAGENTS
ALLYL
ACID
ESTERS
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol800386d