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- W2074300830 abstract "Three new processes for the obtention of pyranosidic dienes type B, and D and homologated conjugated enals A, have been designed in the context of the preparation of useful chiral building blocks from monosaccharides. Addition of vinylmagnesium bromide onto ulose 1, followed by acetal ring opening; benzoate protection at C-4 and C-6; and dehydration of the tertiary hydroxyl group, mediated by thionyl chloride, reveals to be a straigthforward route to diene 11. Analogous dehydration on conformationally rigid 2 was not regioselective and afforded isomeric dienes 3 and 6 in a 1:1 ratio. Addition of 2-lithio-1,3 dithiane onto locked 2,3-anhydropyranoses 21 and 22 followed by unravelling of the S,S-acetal moiety led efficiently to homologated α-enals 26, 27, 31, and 30 and hence to dienes 34, 14, 20 and 13 through Wittig methylenation. Finally α-alkoxyvinyl ethers, prepared either by Wittig-Horner reaction of α-alkoxy-uloses, or by hetero Diels-Alder reaction of conjugated-enals, afforded in good to excellent yields pyranosidic α-enals 37, 42, 43, 44, 50 and 51 on treatment with pyridinium hydrochloride in pyridine or a mixture acetic acid-water (4:1)." @default.
- W2074300830 created "2016-06-24" @default.
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- W2074300830 date "1993-08-01" @default.
- W2074300830 modified "2023-10-18" @default.
- W2074300830 title "Efficient routes to pyranosidic homologated conjugated enals and dienes from monosaccharides" @default.
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- W2074300830 doi "https://doi.org/10.1016/s0040-4020(01)87245-8" @default.
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