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A multifaceted phosphate tether: application to the C1-C14 subunit of dolabelides A-D.

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.

SUBMITTER: Waetzig JD 

PROVIDER: S-EPMC2640944 | biostudies-other | 2008 Jan

REPOSITORIES: biostudies-other

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A multifaceted phosphate tether: application to the C1-C14 subunit of dolabelides A-D.

Waetzig Joshua D JD   Hanson Paul R PR  

Organic letters 20071207 1

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 phospha  ...[more]