Boston University College of Arts & Sciences
Department of Chemistry
The 2011 Novartis Lecture
Development and Application of
Carbon-Carbon Bond Forming Reactions
Abstract:
N-allylhydrazones are useful but under-explored intermediates for the
­synthesis of a diverse range of molecules. By exploring these compounds,
my research group has developed new methods for tandem carbon–carbon
carbon–chlorine bond formation and stereoselective diene synthesis.
­Recent efforts have culminated in the development of a novel Brønsted
acid catalyzed rearrangement that we call a ‘traceless bond construction.’
The general concept of a traceless bond construction, as applied to the
­chemistry of N-allylhydrazones, will be discussed.
Recent research in my group has also shown that silyl bis-enol ethers
are versatile species that undergo oxidative carbon–carbon bond formation
to provide a variety of important structures. Within this context, we have
­developed a merged conjugate addition/oxidative coupling process that
has led to the first enantioselective syntheses of metacycloprodigiosin
and prodigiosin R1. However, application of this strategy to the related
molecule, streptorubin B, was unsuccessful. A completely new approach
to streptorubin B that has revealed previously unknown details into
­elements of stereochemistry inherent to these compounds will be
­reported. Strategic application of oxidative coupling to the synthesis
of enantioenriched axially chiral biaryls will also be presented.
Monday, March 21, 2011
4 p.m. Lecture
Boston University
Department of Chemistry
Life Science & Engineering Building
24 Cummington Street
Auditorium B01
www.bu.edu/chemistry
Dr. Regan J. Thomson
Assistant Professor
Department of Chemistry
Northwestern University
0211 055909
Dr. Regan Thomson grew up in New Zealand, where he
studied chemistry at the University of Auckland before moving
to Canberra, Australia in 1998. Thomson completed his PhD
at the Australian National University under the guidance of
Professor Lewis N. Mander in 2003. He then conducted postdoctoral studies with Professor David A. Evans at Harvard
University until 2006, when he began his independent
­career. Thomson is currently an assistant professor and
the Dow Chemical Company Research Professor in the
Department of Chemistry at Northwestern University,
where his research interests are focused on the development of new reactions and the total synthesis of natural
products. He is the recipient of an NSF CAREER Award
and an Amgen Young Investigator Award.