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Org Lett. 2008 Nov 20;10(22):5313-6. doi: 10.1021/ol802266s. Epub 2008 Oct 28.

Siloxacyclopentenes as dienophile-linked directing groups in intramolecular Diels-Alder reactions.

Author information

1
Department of Chemistry, Scripps-Florida, Jupiter, Florida 33458, USA.

Abstract

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.

PMID:
18954061
PMCID:
PMC2650085
DOI:
10.1021/ol802266s
[Indexed for MEDLINE]
Free PMC Article

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