Yamaguchi-Type Lactonization as a Key Step in the Synthesis of Marine Metabolites: (+)-Luffalactone

A Yamaguchi-type cyclization of 5 and subsequent photochemical oxidation of the furanic ring are the key steps in the first synthesis of the marine metabolite (+)-luffalactone 4 and its epimer at C-16, 16-epi-luffalactone, 27. With this work, we have successfully established the absolute configurati...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 74; no. 20; pp. 7750 - 7754
Main Authors Basabe, Pilar, Bodero, Olga, Marcos, Isidro S, Díez, David, Blanco, Araceli, de Román, Mónica, Urones, Julio G
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.10.2009
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclization
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Oxidation-Reduction
Photochemistry
Physical Sciences
Science & Technology
OXIDATION
INACTIVATION
SESTERTERPENOLIDES
ABSOLUTE-CONFIGURATION
MANOALIDE
NATURAL-PRODUCTS
STEREOCHEMISTRY
ESTERIFICATION
(+)-LIMONIDILACTONE
PHOSPHOLIPASE-A2
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Summary:A Yamaguchi-type cyclization of 5 and subsequent photochemical oxidation of the furanic ring are the key steps in the first synthesis of the marine metabolite (+)-luffalactone 4 and its epimer at C-16, 16-epi-luffalactone, 27. With this work, we have successfully established the absolute configuration of the natural product. The key intermediate 5 was obtained from the easily accessible diacetate 6a/6b.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9013996