Stereospecific formation of tetrahydrofurans from substituted 2,8-Dioxabicyclo[3.2.1]oct-3-ylmethanols (original) (raw)

Stereocontrolled synthesis of 1-acetylen-2,3-di-o-benzyl-tetrahydrofurans, 1,4-anhydro-arabinitol, and α,β-dihydroxy-γ-alkyl-butyrolactones

Chirality, 2003

This article describes a concise and efficient synthesis of 1-acetylen-2,3di-O-benzyl-tetrahydrofurans from tartaric acid esters using as the key step the stereocontrolled cyclization of Co 2 (CO) 6 -complexed propargylic diols. This molecule led to enantiomerically pure 1,4-anhydro-arabinitol and ␣,␤-dihydroxy-␥-alkyl-butyrolactones. In the latter case, the critical methylene oxidation at the oxygen vicinal position was performed by RuO 4 . Chirality 15: 148-155, 2003.

Photo-oxygenation of polyhydroxyalkyl- and glycosyl-furans: 1,3-dipolar cycloaddition reactions of the products

Carbohydrate Research, 1989

nosyl)-Zphenylfuran (lc and Id), 3-acetyl-5-(2,3-di-O-acetyl+-D-erythrofuranosyl)-2-methylfuran (le), %acetyl-5-(2,3-di-@acetyl-cY-D-and-P-u-threofuranosyl)-2-methylfuran (lfand lg) have been transformed, through the corresponding endoperoxides, into 3-C-acetyl-6,7,8,9-tetra-O-acetyl-l,3,4-trideoxy-D-arabino-non-3eno-2,5-diulose (3a), ethyl (E)-2-C-benzoyl-2,3,4-trideoxy-5,6:7,8-di-O-isopropylidene-D-arubino-act-2-en-4-ulosonate (3b), ethyl (E)-5,8-anhydro-2-C-benzoyl-2,3,4-trideoxy-6,7-O-isopropylidene-rwibo-(3~) and-D-arabino-act-2-en-4-ulosonate (3d), 2,3-di-O-acetyl-@-erythro-(4e) and-aD -threo-furanosyl3-C-acetyl-C oxopent-Zenoate (4f), and 3-C-acetyl-7,8-di-O-acetyl-6,9-anhydro-l,3,Ctrideoxy-D-xylo-non-3-eno-2,5-diulose (3g). The above y-diketones and y-ketoesters reacted with methyl diazoacetate to yield 5