Approach to the Synthesis of Cladiell-11-ene-3,6,7-triol

The synthesis of an advanced intermediate in the synthesis of the title compound has been achieved. Key steps include an Ireland−Claisen rearrangement to install the C7 tertiary alcohol stereocenter, an SN2‘ reaction of an alkoxymethyl Cu reagent, and a diastereoselective Re-catalyzed allylic alcoho...

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 17; pp. 3663 - 3665
Main Authors Hutchison, John M, Lindsay, Harriet A, Dormi, Silvana S, Jones, Gavin D, Vicic, David A, McIntosh, Matthias C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.08.2006
Amer Chemical Soc
Subjects
Bridged-Ring Compounds - chemical synthesis
Bridged-Ring Compounds - chemistry
Catalysis
Chemistry
Chemistry, Organic
Copper - chemistry
Cyclization
Diterpenes - chemical synthesis
Diterpenes - chemistry
Furans - chemical synthesis
Furans - chemistry
Molecular Structure
Physical Sciences
Science & Technology
EUNICELLIN DITERPENES
ALLYLIC ALCOHOLS
COPPER REAGENTS
CHEMISTRY
SCLEROPHYTIN-A
DEACETOXYALCYONIN ACETATE
ENANTIOSELECTIVE TOTAL-SYNTHESIS
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Summary:The synthesis of an advanced intermediate in the synthesis of the title compound has been achieved. Key steps include an Ireland−Claisen rearrangement to install the C7 tertiary alcohol stereocenter, an SN2‘ reaction of an alkoxymethyl Cu reagent, and a diastereoselective Re-catalyzed allylic alcohol transposition.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol061072j