501644-58-2Relevant academic research and scientific papers
Enantioselective synthesis of apoptolidin sugars
Crimmins, Michael T.,Long, Alan
, p. 4157 - 4160 (2007/10/03)
(Chemical Equation Presented) The de novo synthesis of the C9 and C27 sugar subunits (2) and (3), respectively, of the potent antitumor agent, apoptolidin, has been accomplished. A titanium tetrachloride-mediated asymmetric anti glycolate aldol addition w
Anti-selective aldol reactions with titanium enolates of N-glycolyloxazolidinethiones
Crimmins, Michael T.,McDougall, Patrick J.
, p. 591 - 594 (2007/10/03)
(Matrix presented). A highly diastereoselective anti aldol addition utilizing a variety of N-glycolyloxazolidinethiones has been developed. Enolization of an N-glycolyloxazolidinethione with titanium (IV) chloride and (-)-sparteine followed by addition of an aldehyde activated with additional TiCl4 resulted in highly anti-selective aldol additions, typically with no observable syn isomers. Allyl-protected glycolates demonstrated the highest levels of selection and yields, although O-benzyl and O-methyl glycolyloxazolidinethiones also performed well.
