Total synthesis of the proposed structure of Rhodobacter sphaeroides lipid A resulting in the synthesis of new potent lipopolysaccharide antagonists

WJ Christ, PD McGuinness, O Asano…

Index: Christ, William J.; McGuinness, Pamela D.; Asano, Osamu; Wang, Yuan; Mullarkey, Maureen A.; Perez, Michel; Hawkins, Lynn D.; Blythe, Todd A.; Dubuc, Gloria R.; Robidoux, Andrea L. Journal of the American Chemical Society, 1994 , vol. 116, # 8 p. 3637 - 3638

Full Text: HTML

Citation Number: 77

Abstract

AOCO 0 4 0 OAOC a Reagents and reaction conditions:(i) DCC/DMAP/CH2Cl2/(R)-3- (((allyloxy) carbonyl) oxy) dccanoic acid/0 OC;(ii) AcOH 8O%/rt;(iii) allyl chloroformate/toluene/pyridine/O OC;(iv) bis (allyloxy)(diisopropylamino) phosphine/THF/1H- tetrazole/rt then-78 OC/mCPBA;(v) 6 M HF/CH&N/rt;(vi) CCl&N/K2CO&t;(vii) TBSCl/imidazole/DMF/Ooc;(viii) phosgene/pyridine/O OC then allyl alcohol;(ix) tin (I1) tris ( ...