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

DOI: 10.1248/cpb.46.217

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Chemical and Pharmaceutical Bulletin p. 217 - 221 (1998)

Update date:2022-08-03

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Authors:

Maezaki, Naoyoshi

Shogaki, Takeshi

Uchida, Masashi

Tokuno, Katsuya

Imamura, Tsuneaki

Tanaka, Tetsuaki

Iwata, Chuzo

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Article abstract of DOI:10.1248/cpb.46.217

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.

Full text of DOI:10.1248/cpb.46.217

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