A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D.
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.
Whitehead
Alan
A
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Waetzig
Joshua D
JD
Thomas
Christopher D
CD
Hanson
Paul R
PR
D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D018942:Macrolides; D009943:Organophosphorus Compounds; C481199:dolabelide A; C481200:dolabelide B; C524147:dolabelide C; C509949:dolabelide D