Abstract:
A facile Lewis-acid-catalyzed method for the synthesis of structurally diverse sesquiterpenoid derivatives
from readily available and abundant 11-membered natural product zerumbone has been developed. Starting from zerumbone, we have developed an efficient cyclization process for the creation of [5.7], [5.8], and [5.8.3] fused-ring systems. This process was exemplified by the selective functionalization of zerumbone; by controlling the conformation of the 11-membered ring, the ring-closing process could be tuned
to afford the fused-ring system of choice.