SOME APPLICATIONS OF RATES OF METHIODIDE FORMATION TO ALKALOID STRUCTURAL DETERMINATION

被引：35

作者：

SHAMMA, M

JONES, CD

WEISS, JA

机构：

[1] Department of Chemistry, The Pennsylvania State University, University Park

来源：

TETRAHEDRON | 1969年 / 25卷 / 18期

关键词：

D O I：

10.1016/S0040-4020(01)82973-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemistry of selagine at C-11 has been determined, and this alkaloid can now be represented by expression IVa. Tetrahydroprotoberberines may exist in any of three different conformations IX, XV, or XVIII. depending upon the substitution pattern at C-1 and C-13. The alkaloids capaurine (XVI) and capaurimine (XVII) exist in conformation XVIII; and no stable B/C trans fused analog of these species can exist. Rates of methiodide formation provide a facile means for differentiating between pavine and isopavine bases, since the latter quaternize at a faster rate. © 1969.

引用

页码：4347 / &

共 28 条

[1] PAVINE .2. THE STRUCTURE OF ISOPAVINE [J].

BATTERSBY, AR ;

YEOWELL, DA .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (MAY) :1988-1991

[2] PAVINE .1. THE STRUCTURE AND CHEMISTRY OF PAVINE [J].

BATTERSBY, AR ;

BINKS, R .

JOURNAL OF THE CHEMICAL SOCIETY, 1955, :2888-2896

[3]

BERSCH HW, 1950, ARCH PHARM WEINHEIM, V283, P36

[4]

BOUGAULT MJ, 1901, B SOC CHIM FR, V25, P857

[5]

BUCK JS, 1924, J CHEM SOC, P1675

[6] MASS SPECTRA OF ISOPAVINE ALKALOIDS STRUCTURE OF AMURENSINE AND AMURENSININE [J].

DOLEJS, L ;

HANUS, V .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1968, 33 (02) :600-&

[7] ALKALOIDS OF AMARYLLIDACEAE .12. AROMATIC OXYGENATION PATTERNS AND STEREOCHEMISTRY OF SOME TRIOXYARYL ALKALOIDS OF HEMIACETAL AND LACTONE SERIES [J].

HAWKSWORTH, WA ;

JEFFS, PW ;

TIDD, BK ;

TOUBE, TP .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAR) :1991-+

[8] STEREOCHEMISTRY OF CORYDALINE AND RELATED ALKALOIDS [J].

JEFFS, PW .

EXPERIENTIA, 1965, 21 (12) :690-&

[9] A RE-EXAMINATION OF STEREOCHEMISTRY OF QUINOLIZIDINE AND METHYLQUINOLIZIDINES THROUGH MEASUREMENT OF THEIR RATES OF QUATERNISATION AND THOSE OF HEXAHYDROJULOLIDINES [J].

JOHNSON, CD ;

JONES, RAY ;

KATRITZK.AR ;

PALMER, CR ;

SCHOFIEL.K ;

WELLS, RJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (DEC) :6797-&

[10] STRUCTURE OF CAPAURIMINE [J].

KAMETANI, T ;

FUKUMOTO, K ;

YAGI, H ;

IIDA, H ;

KIKUCHI, T .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (09) :1178-&

← 1 2 3 →