Poitediol synthesis

This ring expansion when applied to 1 in a synthesis of the sesquiteipene poitediol (3) proceeds in low yield. However, the l-alkynyl-2-alkenylcyclobutanol obtained by addition of lithium acetylide to 1 rearranges to the desired cyclooctadienone 2 in satisfactory yield at 50°. ... 

Similarly, the total synthesis of poitediol is based on the rearrangement of an appropriate norcaranol derivative. With boron trifluoride-diethyl ether complex, nearly quantitative formation of the desired cyclobutanone 72 was observed. ... 

Oxy-Cope rearrangement of acetylene derivatives 42 gives cyclooctadienones1012. The rearrangement of enynol 45 is applied in the synthesis of poitediol. The synthesis of ( )-phorcan-tholide I is achieved from substrate 471128. 

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