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Concise Synthesis of the neo-Clerodane Skeleton of Teucrolivin A Using a Pericyclic Reaction Cascade

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journal contribution
posted on 2006-03-03, 00:00 authored by Steve Arns, Louis Barriault
Herein, we describe the synthesis of advanced intermediate 39 on the path towards the total synthesis of teucrolivin A (3) in 16 steps from commercially available 1,3-cyclohexadiene. We have constructed the trans-decalin core of the natural product 3 as a single diastereomer using a tandem oxy-Cope/Claisen/ene cascade and in doing so have incorporated sufficient functionality to allow completion of the total synthesis.