ALKALOIDS OF PESCHIERA LUNDII (DC) MIERS . ISOLATION AND STRUCTURE ELUCIDATION OF VOACRISTINE PSEUDOINDOXYL AND IBOXYGAINE HYDROXYINDOLENINE

被引:26
作者
HWANG, B
WEISBACH, JA
DOUGLAS, B
RAFFAUF, R
CAVA, MP
BESSHO, K
机构
[1] Smith Kline & French Laboratories, Pennsylvania 19101, Philadelphia
[2] Department of Chemistry, Wayne State University, Michigan 48902, Detroit
关键词
D O I
10.1021/jo01254a033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Voacristine pseudoindoxyl (C22H28N2O5) and iboxygaine hydroxyindolenine (C20H26N2O3) were isolated from Peschiera lundii (D.C.) Miers. Their structures were determined on the basis of spectral data and confirmed by partial synthesis from related alkaloids. In addition, voacangine, coronaridine, voacristine, 20-epivoacristine, iboxygaine, ibogaine, olivacine, and vobasine were found in the same plant. Most of the iboga alkaloids isolated were oxidized 1o the corresponding hydroxyindolenines and rearranged to pseudoindoxyls, several of which were chemically characterized for the first time. © 1969, American Chemical Society. All rights reserved.
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页码:412 / &
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共 19 条
[11]   ISOLATION OF RUPICOLINE AND MONTANINE 2 PSEUDOINDOXYL ALKALOIDS OF TABERNAEMONTANA RUPICOLA BENTH [J].
NIEMANN, C ;
KESSEL, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) :2265-&
[12]  
PERCHERON F, 1959, ANN CHIM, V4, P303
[13]  
PUISIEUX F, 1965, ANN PHARM FR, V23, P33
[14]   ALKALOIDE AUS CONOPHARYNGIA-DURISSIMA STAPF ISOVOACANGIN, CONOPHARYNGIN, CONODURIN UND CONODURAMIN [J].
RENNER, U ;
PRINS, DA ;
STOLL, WG .
HELVETICA CHIMICA ACTA, 1959, 42 (05) :1572-1581
[15]  
SCHNOES HK, 1968, J ORG CHEM, V33, P1225
[16]  
Taylor W. I., 1965, ALKALOIDS, VVIII, P203
[17]  
WEISBACH JA, 1965, CHEM IND-LONDON, P623
[18]  
WEISBACH JERRY A., 1963, JOUR PHARMACEUT SCI, V52, P350, DOI 10.1002/jps.2600520408
[19]   ALKALOIDS OF THE AMARYLLIDACEAE .3. ISOLATION OF 5 NEW ALKALOIDS FROM HAEMANTHUS SPECIES [J].
WILDMAN, WC ;
KAUFMAN, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (05) :1248-1252