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A Multifaceted Phosphate Tether:  Application to the C1−C14 Subunit of Dolabelides A−D

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journal contribution
posted on 03.01.2008, 00:00 by Joshua D. Waetzig, Paul R. Hanson
A phosphate tether approach to the C1−14 subunit of dolabelide is described. The phosphate tether serves a multifaceted role mediating several processes, including (i) diastereotopic differentiation via RCM, (ii) selective CM by imparting Type III behavior to the exocyclic olefin, (iii) regioselective hydrogenation, and (iv) regioselective Pd(0)-catalyzed reductive opening of the bicyclic phosphate. Overall, this strategy uses orthogonal protecting- and leaving-group properties innate to phosphate esters to rapidly assembly the titled subunit.