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

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.

SUBMITTER: Halvorsen GT 

PROVIDER: S-EPMC2650085 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature

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

Halvorsen Geoff T GT   Roush William R WR  

Organic letters 20081028 22

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. ...[more]

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