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Studies Directed Towards the Biosynthesis of the C7N Unit of Rifamycin B: A New Synthesis of Quinic Acid from Shikimic Acid (1991)

Meier, Rose-Marie ; Tamm, Christoph

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 74 (1991), S. 807-818

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The synthesis of quinic acid (4) via epoxide 13, starting from shikimic acid (5), is described (Scheme 1). Treatment of 13 with thiophenol yielded not only 17, but also the γ-lactones 18 and 19 as result of migration of silyl groups within a cis- and trans-diol system. The conversion provides a direct stereoselective epoxidation of a shikimic-acid derivative as well as an alternative pathway for the preparation of 4. A shorter approach via the disilylated epoxide 22 was unsuccessful because the γ-lactone 25 was obtained in place of the desired α-hydroxy ester 24 (Scheme 2).

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19910740415

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