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Deoxy-nitrosugars, 7th communication6th Communication: [1]. Synthesis of methyl shikimate and of diethyl phosphashikimate from D-ribose (1984)

Mirza, Sohail ; Vasella, Andrea

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 67 (1984), S. 1562-1567

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The chain elongation of the deoxy-nitroribose 6 by a Michael addition to the vinyl-phosphonate 7 followed by a solvolysis gave the heptulosephosphonate 11 (87%). From 11, the key intermediates 15 and 16 (77%) were obtained by a highly diastereoselective reduction, followed by detritylation, periodate cleavage, and silylation. Methoxycarbonylation of 15 and 16 gave 17 and 18 which were converted into methyl shikimate (21; 79%) by intramolecular olefination and partial deprotection. Similarly, phosphonoylation of 16 gave 22 (99%) which was transformed into the diethyl phosphashikimate 2 (53% from 6).

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19840670621

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