I= ISOLATION, STRUCTURE ELUCIDATION AND SYNTHETIC STUDIES IN THE FILED OF INDOLE ALKALOIDS
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Title of Thesis
ISOLATION, STRUCTURE ELUCIDATION AND SYNTHETIC STUDIES IN THE FILED OF INDOLE ALKALOIDS

Author(s)
Talat Fatima
Institute/University/Department Details
University f Karachi/ H.E.J. Research Institute of Chemistry
Session
1998
Subject
Chemistry
Number of Pages
187
Keywords (Extracted from title, table of contents and abstract of thesis)
indole alkaloids, rhazya stricta, trachelospermum jasmi noides, of n-benzylsecodine

Abstract
The thesis is divided into two parts. The first part describes the studies on the chemical constituents of Rhazya stricta and Trachelospermum jasmi noides. While the second part deals with the synthesis of N-benzylsecodine. Investigation on the alkaloidal contents on the leaves of R. stricta, have led to the isolation and identification of five new indole bases

(i) Stricticine (86) Tetrahedron lett., 28 (31) 3609 (1987) (ii) Strictazine (89) manuscript in preparation (iii) Rhazizine (97) Tetrahedron, submitted for publication (iv) 15-Hydroxyvincadifformine (98) Phytochemistry accepted for publication (v) Strictimidine (103) manuscript in preparation

The leaves and stems of Trachelospermum jasminoides was investigated for the first time by Atta-ur-Rahman and co-workers. This plant was found to contain indole alkaloid, which led to the isolation of nine bases. (vi) Coronridine (113) Planta medica 1, 57 (1987) (vii) Voacangine (114) Planta medica 1, 57 (1987) (viii) 17-Hydroxy indolenine voacangine (115) Planta medica 54, 364 (1988) (ix) Apparicine (116) Planta Medica, 1, 57 (1987) (x) Conflorine (117) Planta medica, 1, 57 (1987) (xi) 19-Epi-voacangarine (118) Planta medica, 1, 57 (1987) (xii) Ibogaine (119) Planta medica, 54, 364 (1988) (xiii) Tabernaemontanine (120) Planta medica, 54, 364 (1988) (xiv) Vobasine (121) Planta medica, 54, 364 (1988)

Modern spectroscopic techniques including two dimensional NMR experiments (CPSY-45, 2D I-nesolved, NOESY, Hetero COSY, COLOC) were employed to elucidate the structure of the above mentional compounds. DEPT and GSSPE experiments were carried out to determine the multiplicities of the carbon atoms. The stereochemistry at various asymmetric centres was established by extensive noe difference measurements

The second part of the theis deals on the total synthesis of N-benzyl secodine (214). The basic strategy of the synthesis is based on the generation of an indole-2-acrylate unit which makes the use of Friedel-Crafts acylation and a Wittig reaction, I. Pak. Chem. Soc., (accepted for publication).

Download Full Thesis
1187.04 KB
S. No. Chapter Title of the Chapters Page Size (KB)
1 0 Contents 0
93.43 KB
2 1 Part-A-Indole Alkaloids 1
200.96 KB
  1.1 Introduction 1
  1.2 Biosynthesis 5
3 2 Isolation And Structure Elucidation Of Alkaloids From Rhazya Stricta 32
460.77 KB
  2.1 Introduction 32
  2.2 Result And Discussion 34
4 3 Isolation And Structure Elucidation Of Alkaloids From Trachelospermum Jasminoides 94
151.17 KB
  3.1 Introduction 94
  3.2 Result And Discussion 95
5 4 Experimental 118
153.58 KB
  4.1 Isolation Of Alkaloids From The Leaves Of Rhazya Stricta 118
  4.2 Isolation Of Alkaloids From The Leaves And Stems Of Trachelospermum Jasminiodes 127
6 5 Part-B-Total Synthesis Of N-Benzylsecodine 136
189.21 KB
  5.1 Introduction 118
  5.2 Result And Discussion 127
7 6 Experimental 160
91.95 KB
  6.1 Total Synthesis Of N-Benzylsecondine 160
8 7 References 171
130.21 KB
9 8 List Of Publications 188
15.33 KB