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- W2164611427 abstract "Abstract Starting from inexpensive furan and furfuryl alcohol, a noniterative approach to the synthesis of pentadeca-1,3,5,7,9,11,13,15-octols and their derivatives has been developed. The method relies upon the double [4+3]-cycloaddition of 1,1,3-trichloro-2-oxylallyl cation with 2,2'-methylenedifuran and conversion of the adducts into meso and (±)- threo -1,1'-methylenebis ( cis - and trans -4,6-dihydroxycyclohept-1-ene) derivatives. The latter undergo oxidative cleavage of their alkene moieties, generating 5-hydroxy-7-oxoaldehydes that are reduced diastereoselectively into either syn or anti -5,7-diols. Asymmetry is realized using either chiral desymmetrization with Sharpless asymmetric dihydroxylation or by kinetic resolution of polyols using lipase-catalyzed acetylations. All of the possible stereomeric pentadeca-1,3,5,7,9,11,13,15-octols and derivatives can be obtained with high stereoselectivity applying simple operations, thus demonstrating the high stereodiversity of this new, noniterative approach to the asymmetric synthesis of long-chain polyketides." @default.
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- W2164611427 date "2005-01-01" @default.
- W2164611427 modified "2023-10-03" @default.
- W2164611427 title "Noniterative approach to the total asymmetric synthesis of 15-carbon polyketides and analogs with high stereodiversity" @default.
- W2164611427 cites W2091302131 @default.
- W2164611427 doi "https://doi.org/10.1351/pac200577010131" @default.
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