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- W2098795164 abstract "The 2,2′-methylenebis[furan] (1) was converted to 1-{(4R,6S))-6-[(2R)-2,4-dihydroxybutyl]-2,2-dimethyl-1,3-dioxan-4-yl}-3-[(2R,4R)-tetrahydro-4,6-dihydroxy-2H-pyran-2-yl)propan-2-one ((+)-18) and its (4S)-epimer (−)-19 with high stereo- and enantioselectivity (Schemes 1–3). Under acidic methanolysis, (+)-18 yielded a single spiroketal, (3R)-4-{(1R,3S,4′R,5R,6′S,7R)-3′,4′,5′,6′-tetrahydro-4′-hydroxy-7-methoxyspiro[2,6-dioxabicyclo[3.3.1]nonane-3,2′-[2H]pyran]-6′-yl}butane-1,3-diol ((−)-20), in which both O-atoms at the spiro center reside in equatorial positions, this being due to the tricyclic nature of (−)-20 (methyl pyranoside formation). Compound (−)-19 was converted similarly into the (4′S)-epimeric tricyclic spiroketal (−)-21 that also adopts a similar (3S)-configuration and conformation. Spiroketals (−)-20, (−)-21 and analog (−)-23, i.e., (1R,3S,4′R,5R,6′R)-3′,4′,5′,6′-tetrahydro-6′-[(2S)-2-hydroxybut-3-enyl]-7-methoxyspiro[2,6-dioxabicyclo[3.3.1]nonane-3,2′-[2H]pyran]-4′-ol, derived from (−)-20, were assayed for their cytotoxicity toward murine P388 lymphocytic leukemia and six human cancer cell lines. Only racemic (±)-21 showed evidence of cancer-cell-growth inhibition (P388, ED50: 6.9 μg/ml)." @default.
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- W2098795164 date "2004-06-01" @default.
- W2098795164 modified "2023-10-03" @default.
- W2098795164 title "Non-iterative Asymmetric Synthesis of C15 Polyketide Spiroketals" @default.
- W2098795164 cites W575090052 @default.
- W2098795164 doi "https://doi.org/10.1002/hlca.200490136" @default.
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