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Stereoselective Conversion of Aucubin into Polyfunctionalized Tetrahydro‐1 H ‐cyclopenta[ c ]furan Glucosides
Author(s) -
Mouriès Christine,
Deguin Brigitte,
Koch Michel,
Tillequin François
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390005
Subject(s) - chemistry , furan , synthon , stereoselectivity , phthalimide , mitsunobu reaction , triphenylphosphine , stereochemistry , organic chemistry , medicinal chemistry , catalysis
Mitsunobu reaction of 2′,3′,4′,6′,10‐penta‐ O ‐pivaloylaucubin ( 6 ) with phthalimide, triphenylphosphine, and diethyl azodicarboxylate gave (6 R )‐6‐phthalimido‐perpivaloylbartsioside ( 10 ) ( Scheme 1 ). Selective oxidation reactions performed with perpivaloylaucubin ( 12 ) yielded (1 R )‐ and (1 S )‐3( β ‐ D ‐glucopyranosyloxy)‐1 H ‐cyclopenta[ c ]furan‐1‐carboxaldehydes 13 and 14 respectively ( Scheme 2 ). Similarly, perpivaloyl‐6‐epiaucubin ( 9 ) and 10 afforded the corresponding (1 S )‐carboxaldehyde 15 and (1 R )‐carboxaldehyde 16 , respectively. The protected cyclopentafuran glycosides obtained in this way are versatile synthons, which may prove useful for further chemical diversification.