1-Methoxy-3-(2-nitrovinyl)indole (4) functions as an electrophile and reacted with various nucleophiles regioselectively at the 2-position. Employing allyl alkoxides as nucleophiles, a novel synthetic method of pyrrolo[2,3-b]indoles has been elaborated. Utilizing the method, the synthesis of (±)-debromofIustramine B (10b) was achieved.