2000
DOI: 10.1002/(sici)1099-0690(200005)2000:9<1741::aid-ejoc1741>3.0.co;2-w
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Synthesis of Heptano Bridged Pyranoside Derivatives
Abstract: Addition of dichlorocarbene to the glycal (±±)‐2 followed by cyclopropyl‐allyl rearrangement leads to the chloro‐2H‐pyran (±±)‐4. Oxidation of (±±)‐4 and reduction of the obtained hydroxypyranone (±±)‐5 gave the methyl pyranoside (±±)‐6. The relative configuration of (±±)‐6 was established by X‐ray structural analysis of the corresponding acetate (±±)‐7. The synthesis of the optically active starting materials (+)‐2 and (−)‐2 is also reported.
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Cited by 9 publications
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