Etherification allyl rearrangement

For the synthesis of the intermediate of the sesquiterpene ( )-ceratopicanol, the secondary allylic alcohol 7 was converted to a new alcohol 8 via one-pot etherification, Claisen rearrangement and reduction with LiAlH4 (Eq. 3.1.7) [12]. This trans-... 

Utilization of a selenium-initiated electrophilic cyclization (lactonization, etherification) in conjunction with a [2,3] sigmatropic selenoxide rearrangement provided a convenient, stereoselective access to highly substituted bicyclic lactones or ethers (entries 6-8)25-29. The electrophilic addition of phenylselenenyl halogenides to dienes can occur in a 1,2-(anti)-or 1,4-fashion furnishing allylic selenides in both cases. 

On heating methylbutenol (9.21) with 2-methoxypropene (9.27) (which is the methyl enol ether of acetone), a /ra .v-etherification occurs with the elimination of methanol and the formation of the allyl vinyl ether (9.28). This ether is perfectly set up for a Claisen rearrangement, which it undergoes, to produce methylheptenone (9.5). 

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