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. 2008 Jan 3;10(1):109-12.
doi: 10.1021/ol7025944. Epub 2007 Dec 7.

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

Joshua D Waetzig  1 , Paul R Hanson
Affiliations

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

Joshua D Waetzig et al. Org Lett. .

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.

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Figures

Scheme 1
Scheme 1
Retrosynthetic Analysis of Dolabelide
Scheme 2
Scheme 2
Synthesis of CM Partner 2.3
Scheme 3
Scheme 3
CM Studies with Bicyclic Phosphate 5
Scheme 4
Scheme 4
Selective Phosphate Cleavage in the Synthesis of Phosphate 17
Scheme 5
Scheme 5
Synthesis of the C1-C15 Subunit of Dolabelide
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