A Multifaceted Phosphate Tether:  Application to the C15−C30 Subunit of Dolabelides A−D

Construction of the C15−C30 subunit of dolabelide utilizing a temporary phosphate tether is described. Two routes are reported that make use of the orthogonal protecting- and leaving-group properties innate to phosphate esters. One route relies on a selective terminal oxidation, while a second utili...

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Bibliographic Details
Published inOrganic letters Vol. 10; no. 7; pp. 1421 - 1424
Main Authors Whitehead, Alan, Waetzig, Joshua D, Thomas, Christopher D, Hanson, Paul R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.04.2008
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
Organophosphorus Compounds - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
ACTIVATION
ENANTIOSELECTIVE SYNTHESIS
REDUCTION
FRAGMENT
AURICULARIA
CARBOALUMINATION
ALDEHYDES
STEREOSELECTIVE-SYNTHESIS
EFFICIENT
PROTECTED SYN 1,3-DIOLS
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Summary:Construction of the C15−C30 subunit of dolabelide utilizing a temporary phosphate tether is described. Two routes are reported that make use of the orthogonal protecting- and leaving-group properties innate to phosphate esters. One route relies on a selective terminal oxidation, while a second utilizes a CM/selective hydrogenation sequence. Both routes depend on a highly regio- and diastereoselective cuprate addition to set the requisite stereochemistry at C22.
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/ol8001865