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).