Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach

Article abstract of DOI:10.1016/0968-0896(96)00018-1

Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5β-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5β-cholestane skeleton, 1b with the 5β-androstane skeleton, 1c with a fluorine substituent instead of the chlorine and 1d with a β-D-galactopyranose instead of the β-D-glucopyranose of the original pheromone. Their bioassay shows that 1a and 1c are active, while 1b and 1d are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active.