A Formal Synthesis of the Auriside Aglycon

A highly convergent formal synthesis of the auriside aglycon was achieved. An indene-based thiazolidinethione chiral auxiliary was used for the construction of both the C1−C9 and C10−C17 fragments via acetate aldol reactions. A Meinwald reaction was utilized to install the stereocenter at C2, and a...

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Bibliographic Details
Published inOrganic letters Vol. 10; no. 11; pp. 2191 - 2194
Main Authors Tello-Aburto, Rodolfo, Olivo, Horacio F
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.06.2008
Amer Chemical Soc
Subjects
Acetates - chemistry
Aldehydes - chemistry
Chemistry
Chemistry, Organic
Macrolides - chemical synthesis
Macrolides - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Thiazolidines - chemistry
CALLIPELTOSIDE-A
STEREOCHEMICAL REASSIGNMENT
HARE DOLABELLA-AURICULARIA
ASYMMETRIC ALDOL ADDITIONS
STEREOCONTROLLED TOTAL-SYNTHESIS
N-ACYL OXAZOLIDINONES
ACETYLENIC ALDEHYDES
CYTOTOXIC MACROLIDE GLYCOSIDES
RELATIVE CONFIGURATION
CHIRAL AUXILIARY
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Summary:A highly convergent formal synthesis of the auriside aglycon was achieved. An indene-based thiazolidinethione chiral auxiliary was used for the construction of both the C1−C9 and C10−C17 fragments via acetate aldol reactions. A Meinwald reaction was utilized to install the stereocenter at C2, and a conjugated addition to an ynone was used to construct the C9−C11 enone.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol8005908