172805-64-0Relevant academic research and scientific papers
3,4-Dehydro-2-hydroxy-6-(2-phenethyl)tetrahydropyran. 1,3-Acyclic diastereoselection in reaction with MeOH and its application in the synthesis of a racemic mevinolin analog
Yadav, Veejendra K.,Kapoor, Kamal K.
, p. 8 - 13 (2007/10/03)
3,4-Dehydro-2-hydroxy-6-(2-phenethyl)tetrahydropyran (6) and its dimer (7) both react with MeOH in the presence of a catalytic amount of conc. HCl to provide 2,4-bismethoxy-6-(2-phenylethyl)tetra-hydropyran with a decent level of 1,3-acyclic diastereoselection in favour of the 4,6-trans derivative (9a). The ratio of the arabino (9a) and xylo (9b) structures was an unprecedented 4:1. Models to account for the observed diastereoselectivity are discussed. Further transformation to the 2-oxo derivative and unmasking of the 4-OH function provide a rapid entry into a racemic mevinolin analog (14).
