Huang, Z: Organometallic Catalysis and Its Application To Th

Negishi coupling has been serving as one of the powerful methods for the construction of C-C bond since its first discovery in 1976. Many research groups have utilized Negishi coupling to synthesize various types of natural products or complex organic compounds as the pivotal step. To overcome a long-standing synthetic challenge of preparing (Z)-trisubstituted alkenes, the author developed a novel methodology for the first time, as depicted in chapter one, which has been successfully applied to the synthesis of discodermolide, (-)-callystatin A and archazolid A and B natural products, and most importantly, to the total synthesis of (6E,10Z)-O-Methylmyxalamide D, for the first time. As discussed in chapter two, a rather novel method was provided to prepare HZrCp2Cl, which has been employed in the synthesis of conjugated oligoenes. In Chapter three, thanks to the combination of lipase-catalyzed acetylation and Zr catalysis, the synthetic power of Zr-catalyzed Asymmetric Carboalumniation of Alkenes (ZACA) has been eloquently demonstrated through the synthesis of many natural products, which seem to be mission impossible if only the ZACA was used alone.