An enantioselective total synthesis of the polycyclic diterpene (+)-chatancin, a potent PAF antagonist, is reported. Proceeding in seven steps from dihydrofarnesal, this synthetic route was designed to circumvent macrocyclization-based strategies to complex, cyclized cembranoids. The described synthesis requires only six chromatographic purifications, is high yielding, and avoids protecting-group manipulations. An X-ray crystal structure of this fragile marine natural product was obtained.
Keywords: asymmetric synthesis; biomimetic synthesis; cycloaddition reaction; natural products; terpenes.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.