Accessing Polycyclic Terpenoids from Zerumbone via Lewis Acid Catalyzed Synthetic Strategies
SHARATHNA (P), MEENU (M T), DHANYA (B P), GOPALAN (G), SASIKUMAR (P), KRISHNAN (R S), RADHAKRISHNAN (K V)
zerumbone; zerumbone epoxide; zerumbal; zerumbenone; Lewis acid catalysis; cyclization; polycyclic terpenoids
We herein disclose an effective strategy for the synthesis of [5.3.0] and [6.3.0] fused polycyclic terpenoids, which are important structural elements of natural products and biologically active compounds. The method comprises of Lewis acid catalyzed interrupted Nazarov cyclization of zerumbone derivatives such as zerumbone epoxide, triazole-appended zerumbone, zerumbal, and zerumbenone with a wide substrate scope with different indoles. Zerumbone epoxide furnished [5.3.0] and [6.3.0] fused structurally diverse sesquiterpenoids and all other zerumbone derivatives furnished the [6.3.0] fused motifs.