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ENANTIOSPECIFIC SYNTHESIS OF SHIKIMIC ACID FROM D-MANNOSE - FORMATION OF A CHIRAL CYCLOHEXENE BY INTRAMOLECULAR OLEFINATION OF A CARBOHYDRATE-DERIVED INTERMEDIATE

Abstract:
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- trifluoromethylsulphonyl-α-D-lyxofuranoside by the sodium salt of t-butyl dimethoxyphosphorylacetate provides a rare example of substitution at the C-5 position of a furanose derivative by a carbanion.
Publication status:
Published

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Publisher copy:
10.1039/p19840000905

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Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
5
Pages:
905-908
Publication date:
1984
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
URN:
uuid:5391ff7b-5d45-478e-9465-990c9cd8c3a3
Source identifiers:
42319
Local pid:
pubs:42319
Language:
English

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