Approach to the synthesis of Cladiell-11-ene-3,6,7-triol

by Hutchison, John M.; Lindsay, Harriet A.; Dormi, Silvana S.; Jones, Gavin D.; Vicic, David A.; McIntosh, Matthias C.

The synthesis of an advanced intermediate in the synthesis of the title compound has been achieved. Key steps include an Ireland - Claisen rearrangement to install the C7 tertiary alcohol stereocenter, an S(N)2' reaction of an alkoxymethyl Cu reagent, and a diastereoselective Re-catalyzed allylic alcohol transposition.