By R. C. Anderson Ph. D., B. Sc., Prof. B. Fraser-Reid, Dr. H. Jones, Dr. T. Kasai, Prof. P. O. Larsen, Prof. S. Liaaen-Jensen, Dr. G. H. Rasmusson (auth.), Dr. W. Herz, Prof. Dr. H. Grisebach, G. W. Kirby Sc. D. (eds.)
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Extra info for Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products
A. LAIDLER, J. F. STODDARD, J. B. WOLSTENHOLME, and G. H. JONES: Enantiomeric Differentiation by a Chiral Symmetrical Crown Derived from L-Iditol. Carbohyd. Res. 57, C 17 (1977); LAIDLER, C. , and 1. F. STODDARD: Chiral Asymmetrical Crown-Ethers. Carbohyd. Res. 55, C 1 (1977); LAIDLER, D. , and J. F. STODDARD: Stereoselectivity in Complexation of Primary Alkylammonium Cations by the Diastereotopic Faces of Chiral Asymmetric Crowns. Chern. Commun. 1977, 481. 14. DEFAYE,1.. and 1. HILDESHEIM: Syntheses dans la Serie des 2,5-Anhydrides des Sucres.
On the basis of literature precedents (58) it was hoped that hydrolysis of (149) would produce a nitrocyc1itol directly. This turned out to be the case although the intervening hemiacetal (150) could be isolated by judicious crystallisation. However the nitrocyc1itol was not the desired substance (151) but the stereoisomer (153a). This adverse course of events could perhaps be avoided by employing the glyoxylate ester (155) (Scheme 36), for which di-condensation on the same nitromethyl group would lead to the formation of two six-membered rings in (156).
C'••),O • 0 - ° / OMe H2 S0 4 HOAc OC~Ph (149) r:~::OA' ~