Secokotomolide A and Secomahubanolide A were isolated from cinnamoum ketones and machilus zuihoensis respectively. Secokotomolide A was found to induce significant cell death in the human HeLa cell line by apoptotic-realted DNA damage. Secomahubanolide A shows marginal cytotoxicity against NUGC and HONE-1 cancer cell lines.
The enantioselective synthesis of Secokotomolide A and Secomahubanolide A, has been accomplished from the readily available chiral (Z)-β-iodo Morita-Baylis-Hillman ester (1) as a key intermediate. Asymmetric three component coupling reaction furnished (Z)-β-iodo MBH ester (1) in high enantioselectivity. Additional few steps afforded both natural products in high overall yield.