Synthetic studies on slaframine

Abstract

Thjs thesis is concerned with the prelIminary studies in the synthesis of an indolizine alkaloid, slaframine. A Wittig reaction of 3-carbethoxypropyltriphenylphosophonium iodide (43) with 4-pentenal (44) gave ethyl-(Z)-4,8-nonadienoate (45). Hydrolysis of this product gave the unsaturated acid (46) which was then converted into acid chloride (47), acylazide (48), isocyanate (49) and finally l-amino-3,7-octadiene (50) . The primary amino group of (50) was protected by forming trifluoroacetate derivative (51). 1- Amino-3,7-octadiene was converted in N-(Benzyloxycarbonyl)-3,7-octadiene (52) which was finally converted into epoxide (53). Other related studies involved: (1) preparation of 1,2-oxidocyclohex-4-ene (54) which was converted into trans-2-azidocyclohex-4-enol (55). The secondary alcohol group was protected by forming acetate derivative (56). A tetrahydropyranyl derivative (57) was also prepared.