A Multifaceted Phosphate Tether:
Application to the C1-C14 Subunit of
Dolabelides A-D
Joshua D. Waetzig andPaul R. Hanson*
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive,
Lawrence, Kansas 66045
phanson@ku.edu
Received October 25, 2007
Abstract:
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.
