A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D.

Org Lett

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.

Published: April 2008

Construction of the C15-C30 subunit of dolabelide utilizing a temporary phosphate tether is described. Two routes are reported that make use of the orthogonal protecting- and leaving-group properties innate to phosphate esters. One route relies on a selective terminal oxidation, while a second utilizes a CM/selective hydrogenation sequence. Both routes depend on a highly regio- and diastereoselective cuprate addition to set the requisite stereochemistry at C22.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2641022PMC
http://dx.doi.org/10.1021/ol8001865DOI Listing

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