ORGANOMETALLIC CATALYSIS AND ITS APPLICATION TO THE TOTAL SYNTHESIS

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.

Autorentext

Zhihong Huang, 2008-Present, Post-doctorate in K. C. Nicolaou's group, TheScripps Research Institute;2003-2008, PHD in Prof. Negishi's group, Purdue University;2001-2003, MS in Prof. Montchamp's group, Texas Christian University;1997-2001, BS in Peking University, Beijing, P. R. China

Klappentext

Negishi coupling has been serving as one of thepowerful methods for the construction of C-C bondsince its first discovery in 1976. Many researchgroups have utilized Negishi coupling to synthesizevarious types of natural products or complex organiccompounds as the pivotal step. To overcome along-standing synthetic challenge of preparing(Z)-trisubstituted alkenes, the author developed anovel methodology for the first time, as depicted inchapter one, which has been successfully applied tothe synthesis of discodermolide, (-)-callystatin Aand archazolid A and B natural products, and mostimportantly, to the total synthesis of(6E,10Z)-O-Methylmyxalamide D, for the first time. Asdiscussed in chapter two, a rather novel method wasprovided to prepare HZrCp2Cl, which has been employedin the synthesis of conjugated oligoenes. In Chapterthree, thanks to the combination of lipase-catalyzedacetylation and Zr catalysis, the synthetic power ofZr-catalyzed Asymmetric Carboalumniation of Alkenes(ZACA) has been eloquently demonstrated through thesynthesis of many natural products, which seem to bemission impossible if only the ZACA was used alone.