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. 2007 May 24;9(11):2243-6.
doi: 10.1021/ol070858u. Epub 2007 May 5.

Intramolecular Diels-Alder reactions of siloxacyclopentene constrained trienes

Geoff T Halvorsen  1 , William R Roush
Affiliations

Intramolecular Diels-Alder reactions of siloxacyclopentene constrained trienes

Geoff T Halvorsen et al. Org Lett. .

Abstract

The synthesis of siloxacyclopentene-constrained trienes 7 and 10 and studies of their IMDA cycloadditions are described. The use of appropriately chosen thermal or Lewis acid conditions allows for cycloadducts 3-6 to be obtained with high levels of diastereoselectivity. These adducts possess trans-relationships between the hydroxyl group and the adjacent ring fusion proton, a stereochemical relationship not previously attainable in IMDA reactions.

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Figures

Scheme 1
Scheme 1
Steric Directing Group Strategy
Scheme 2
Scheme 2
Siloxacyclopentene Directing Group Strategy for IMDA Reactions
Scheme 3
Scheme 3
Synthesis of Trienes 7a and 10a
See this image and copyright information in PMC

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