ENANTIOSPECIFIC SYNTHESIS OF SHIKIMIC ACID FROM D-MANNOSE - FORMATION OF A CHIRAL CYCLOHEXENE BY INTRAMOLECULAR OLEFINATION OF A CARBOHYDRATE-DERIVED INTERMEDIATE
An enantiospecific synthesis of (-)-shikimic acid from D-mannose in an overall yield of 39% is described, in which the key step is an intramolecular Wadsworth-Emmons olefination reaction of a phosphonate. Nucleophilic displacement of triflate from benzyl 2,3-O-isopropylidene-5-O- trifluoromethylsulp...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
1984
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