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A Short Synthesis of ( S )‐5‐Hydroxy‐2‐penten‐4‐olide from D ‐Mannitol via 2,3‐ O ‐Isopropylidene‐ D ‐glyceraldehyde
Author(s) -
Häfele Brigitte,
Jäger Volker
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870116
Subject(s) - chemistry , d mannitol , glyceraldehyde , wittig reaction , mannitol , acetonide , yield (engineering) , stereochemistry , organic chemistry , medicine , materials science , surgery , triamcinolone acetonide , metallurgy , dehydrogenase , enzyme
( S )‐5‐Hydroxy‐2‐penten‐4‐olide ( 5 ) was synthesized in three steps starting from D ‐mannitol bis(acetonide) ( 1 ), via D ‐glyceraldehyde acetonide ( 2 ) by Z ‐selective Wittig reaction, acid‐catalyzed lactonization and crystallization with a total yield of 40%.