High diastereoselectivity in Claisen rearrangement in a sterically congested cyclopentane system. Total synthesis of (±)-β-necrodol (cas 104086-70-6)

Add time:08/02/2019    Source:sciencedirect.com

Total synthesis of the monoterpene β-necrodol has been accomplished. The key step involves an ortho-ester Claisen rearrangement in a highly sterically congested cyclopentane derivative resulting in a high level of 1,3-trans diastereoselection. A novel photo-induced decarboxylation of the obtained γ,δ-unsaturated acid afforded β-necrodol.

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