Stereospecific synthesis of racemic cis- and trans-6-trifluoromethylshikimic acids
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1281-1287
- https://doi.org/10.1039/p19900001281
Abstract
Two ‘unnatural’ derivatives of shikimic acid, cis- and trans-6-trifluoromethylshikimic acid, have been synthesized in their racemic forms via the base-promoted opening of furan Diels–Alder adducts bearing a CF3 group. The relative stereochemistry of the trans-diastereoisomer has been confirmed by an X-ray analysis of its t-butyl ester.This publication has 2 references indexed in Scilit:
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- Synthesis of "iso-EPSP" and evaluation of its interaction with chorismate synthaseJournal of the American Chemical Society, 1986