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A stereoselective one-pot synthesis of perhydro-7a-hydroxy-7-phenylthiofurano[3,2-b]pyran via an Acid-catalysed deprotection/double cyclisation/rearrangement sequence

✍ Scribed by Neil Edwards; Jacqueline A. Macritchie; Philip J. Parsons


Book ID
104259194
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
186 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis


Treatment of 1,3-bis-[(tert-butyldimethylsilyloxy)ethyl]-1-phenylsulfinyl-1,2-propadiene with aqueous I-IF in acetonitrile :ed to the formation of the rifle compound as one diastereoisomer (from NMR analysis). The reaction was carried out under thermodynamic conditions, and underwent a double deprotection/double cyclisation/rearrangement sequence.