Research Blog

Macrocyclic furanobutenolide-derived cembranoids (FBCs) are the biosynthetic precursors to a wide variety of highly congested and oxygenated polycyclic (nor)diterpenes (e.g. plumarellide, verrillin, and bielschowskysin). These architecturally complex metabolites are thought to originate from site-selective oxidation of the macrocycle backbone and a series of intricate transannular reactions. Yet the development of a common biomimetic route has been hampered by a lack of synth

Bielschowskysin ( 1 ), the flagship of the furanocembranoid diterpene family, has attracted attention from chemists owing to its intriguing and daunting polycyclic architecture and medicinal potential against lung cancer. The high level of functionalization of  1  poses a considerable challenge to synthesis. Herein, a stereoselective furan dearomatization strategy of furanocembranoids was achieved via the intermediacy of chlorohydrins. The stereochemical course of the kinetic

Chemical investigation of the MeOH extract from the gorgonian Pseudopterogorgia americana  afforded two rare sterols, ameristerenol A ( 1 ) and B ( 2 ), both 9,11-secosterols possesses a seven-membered cyclic enol-ether in ring C, and ameristerol A ( 3 ) is the first example of a naturally occurring 9,11-secosterol containing a gorgosterol side chain with a C-24(28) double bond. Ameristerenol A ( 1 ) was converted to the sterol derivatives 4 – 6  to provide additional chemica