A multifaceted phosphate tether: application to the C1-C14 subunit of dolabelides A-D.
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.
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Joshua D
JD
Waetzig
Paul R
PR
Hanson
D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*
D004224:Diterpenes; D018942:Macrolides; D009943:Organophosphorus Compounds; C481199:dolabelide A; C481200:dolabelide B; C524147:dolabelide C; C509949:dolabelide D