Partial synthesis of (±)-pranferol

PARTIAL SYNTHESIS A. Z. A b y s h e v OF ( ± ) - P R A N F E R O L a n d P. UDC 577.15/17:582.89 P. Denisenko The present paper gives the results of a partial synthesis of (*)-pranferol. By the reduction of isoxypeucedanin, obtained by the isomerization of natural oxypeucedanin with 20% sulfuric acid, in methanol with sodium tetrahydroborate we obtained substance (I), C16HI605, mp 111-112° C (from benzene), [a]~ ~- 0 ° (chloroform), R f 0.66 (A1203 of activity grade II in the ethyl acetate system). The IR spectrum of (I) conicided completely with that for pranferol [1]. A mixture with an authentic sample gave no depression of the melting point. The acetylation of (I) with acetic anhydride in pyridine formed an acetyl derivative (II), C18H~806, mp 116.5-117.5° C (from petroleum ether), Rf 0.86 [A1203 , activity grade II, ethyl a c e t a t e - b e n z e n e (1:2) system] In the IR spectrum of the latter the hydroxy group absorption band had disappeared and in addition to the band of the C-----Ogroup of an a-pyrone ring (1730 cm -1 ) the absorption band of an ester carbonyl group had appeared (1740 cm-1). LITERATURE 1. CITED G. A. Kuznetsova, A. Z. Abyshev, M. E. Perel'son, Yu. N. Sheinker, and G. Yu. Pek, Khim. Prirodn. Soedin., 2, 310 (1966). Leningrad Sanitary-Hygienic Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 4, p. 522, July-August, 1972. Original article submitted March 18, 1971. O 1973 Consultants Bureau, a division o[ Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. All rights reserved. This article cannot be reproduced [or any purpose whatsoever without permission of the publisher. A copy of this article is available from the publisher for $15.00. 498  (...truncated)