204589-34-4Relevant academic research and scientific papers
1,6-Asymmetric induction utilizing Asymmetric desymmetrization by diastereoselective C-O bond fission of the 4-substituted bicyclic acetal: Application to a synthesis of (-)-frontalin
Maezaki, Naoyoshi,Shogaki, Takeshi,Uchida, Masashi,Tokuno, Katsuya,Imamura, Tsuneaki,Tanaka, Tetsuaki,Iwata, Chuzo
, p. 217 - 221 (2007/10/03)
1,6-Asymmetric induction was achieved in the acid-induced diastereoselective acetal cleavage reaction of a 4-substituted bicyclic acetal 8 bearing a chiral sulfinyl group. On treatment with titanium tetrachloride and 2,6-disubstituted pyridine bases, 8 gave a synthetically versatile 3,3-disubstituted dihydropyran derivative 9a with moderate diastereoselectivity. The utility of this chiral synthon was successfully demonstrated by a formal synthesis of (-)-frontalin.
