Siloxacyclopentenes as Dienophile-Linked Directing Groups in Intramolecular Diels−Alder Reactions

The synthesis and intramolecular Diels−Alder reactions of trienes 5 and 6 with a siloxacyclopentene-constrained dienophile are described. These reactions provide the primary cycloadducts 7 and 8 with high diastereoselectivity. These cycloadducts possess trans-relationships between the ring fusion pr...

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Bibliographic Details
Published inOrganic letters Vol. 10; no. 22; pp. 5313 - 5316
Main Authors Halvorsen, Geoff T, Roush, William R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.11.2008
Amer Chemical Soc
Subjects
Acetals - chemistry
Chemistry
Chemistry, Organic
Cyclopentanes - chemistry
Ethylene Glycol - chemistry
Physical Sciences
Polyenes - chemistry
Science & Technology
Siloxanes - chemistry
Stereoisomerism
BOTTOM-HALF
ENANTIOSELECTIVE SYNTHESIS
STEREOSELECTIVITY
STEREOCONTROL
(-)-SPINOSYN-A
GROUP STRATEGY
CHLOROTHRICOLIDE
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Summary:The synthesis and intramolecular Diels−Alder reactions of trienes 5 and 6 with a siloxacyclopentene-constrained dienophile are described. These reactions provide the primary cycloadducts 7 and 8 with high diastereoselectivity. These cycloadducts possess trans-relationships between the ring fusion proton and the adjacent C(1) alkoxy group and can be further elaborated to alcohols 9 and 11 (via protiodesilylation) or to 10 and 12 (via Fleming−Tamao oxidation) depending on the substitutent R.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol802266s