James H. Rigby
Organic (Organic Synthesis)
B.S., Case Western Reserve University, 1973
Ph.D., University of Wisconsin-Madison, 1977
Swiss NSF Postdoctoral Fellow, ETH-Zürich,1977-78
NIH Post-Doctoral Fellow, Columbia University, 1978-9
Our research group is engaged in a wide variety of problems directed toward the total synthesis
of pharmacologically active natural products. Several target molecules of current interest in
the group are shown below. In addition to pursuing total synthesis the group is focused on
developing novel synthetic methodology. For example, considerable effort has been committed
to an investigation of chromium(0)-promoted higher-order cycloaddition reactions, which
comprise a class of potentially very powerful transformations for constructing complex cyclic
structures. Processes involving efficient [6π+4π] and [6π+2π] cycloadditions have been
brought to practice recently in our laboratories, and targets such as the steroid, (+)-estradiol
and the tropane alkaloid, (+)-ferruginine have been prepared using this technology. Most
recently, a novel and very powerful chromium(0)-mediated multicomponent cycloaddition has
been discovered in our laboratories which is proving to be an important addition to the synthetic
armory. These multicomponent transformations are uniquely capable of producing
rapid increases in molecular complexity, including the creation of considerable stereochemical
Our group is also actively engaged in studying novel reaction pathways that
are characteristic of vinyl isocyanates. This intriguing functionality has proven
to be a powerful and versatile building block for alkaloid synthesis. Numerous
4+2 and 4+1 cycloaddition processes have been discovered in this context and
molecules such as the anticancer alkaloids, (+)-pancratistatin and (±)-tazettine
have been synthesized with this chemistry. Recently, novel reactive intermediates
known as nucleophilic carbenes have been found to be potent reaction
partners in combination with isocyanates to deliver structurally and functionally
elaborate advanced intermediates for alkaloid synthesis.
Rigby, J. H.; Wang, Z. “Synthesis of Highly
Substituted Cyclopentenones via the [4 + 1]
Cycloaddition of Nucleophilic Carbenes and
Vinyl Ketenes”, Org. Lett. 2003, 5, 263–264.
Rigby, J. H.; Bazin, B.; Meyer, J. H.; Mohammadi,
F. “Synthetic Studies on the Ingenane
Diterpenes. An Improved Entry into a trans-
Intrabridgehead System”, Org. Lett. 2002, 4,
Rigby, J. H.; Kondratenko, M. A.; Fiedler, C.
“Preparation of a Resin-Based Chromium
Catalyst for Effecting [6 + 2] Cycloaddition
Reactions”, Org. Lett. 2000, 2, 3917–3919.
Rigby, J. H.; Maharoof, U. S. M.; Mateo, M. E.
“Studies on the Narciclasine Alkaloids: Total
Synthesis of (+)-Narciclasine and (+)-
Pancratistatin”, J. Am. Chem. Soc. 2000, 122,
Rigby, J. H.; Laurent, S.; Dong, W.; Danca, M.D.
“Bis(alkylthio)carbenes as Novel Reagents for
Organic Synthesis”, Tetrahedron 2000, 56,