Acta Chimica Sinica ›› 1961, Vol. 27 ›› Issue (2): 97-105. Previous Articles     Next Articles

贝母植物碱研究 ⅩⅢ.西贝素中仲醇羟基及羰基的位置和A,B环的立体化学

刘铸晋1, 陆仁荣1, 何凤珍1, 朱子清2, 黄文魁2   

  1. 1. 中国科学院有机化学研究所;
    2. 兰州大学化学系
  • 投稿日期:1959-07-31 发布日期:2013-06-03

A STUDY OF FRITILLARIA ALKALOIDS XIII.THE CHEMISTRY OF SIPEIMINE (IMPERIALIN)THE LOCATION OF THE SECONDARY HYDROXYL AND THE CARBONYL GROUPS AND THE STEREOCHEMISTRY OF RINGS A AND B

LIU CHU-TSIN1, LOH JEN-YUNG1, HO FUN-ZWUN1, CHU TZE-TSIN2, HWANG WEN-KEUI2   

  1. 1. Institute of Organic Chemistry, Academia Sinica;
    2. Department of Chemistry, Lanchow University
  • Received:1959-07-31 Published:2013-06-03

A survey of the molecular rotation data and an examination of the characteristics of the UV absorption spectrum of desoxosipeimone (desoxodihydroimperialon, Ⅱ), coupled with biogenetic considerations, appear to favour the location of the secondary hydroxyl group in sipeimine (imperialin) at C-3.The carbonyl group of sipeimine is tentatively assigned to C-6 in order to account for the unusual chemical and spectral properties of anhydrosipeimine (Ⅹ), which seems to be-have like a cyclopropyl ketone.In the meantime, an extensive study of existing rotation data indicates that position-6 is equally acceptable as position-7 as the site of the carbonyl.The latter position has been favoured by Morgan and Barltrop[11].The location of the tertiary hydroxyl group and the stereochemistry of the rings A and B are discussed.The structure of sipeimine (imperialin) is provisionally presented as (XIV).