James B Hendrickson
Professor of Chemistry
Ph.D., Harvard University
781-736-2520
hendrickson@brandeis.edu
The synthesis of organic molecules has
long been a major activity of organic chemistry, closely linked to
biochemistry for it involves the synthesis of natural products and or
test molecules for examining the parameters of biological reactions.
Nevertheless, it is astonishing how little we know about the right way
to design a synthesis of a new molecule. It is easily shown that there
are literally millions of different routes possible, from different
starting materials, for the synthesis of any substance of interest, but
there has traditionally been no clear protocol to follow to design the
best one before going into the laboratory to try it.
We have been engaged for some years in creating a logic for
synthesis design, which has hitherto been only an art in the midst of
the otherwise systematic science of organic chemistry. This has led to
the creation of the computer program SYNGEN which embodies logical
principles to provide the optimal synthetic sequences for any target
molecule, and has already had considerable success. This program of
computerizing organic chemistry logic welcomes young professionals with
an interest in combining the expertise of computers with that of
organic chemistry. Furthermore, it is of particular interest also for
those who wish to pursue the laboratory execution of these syntheses,
since they may expect to derive especially short routes to molecules of
biological or medical interest from the computer and pursue these in
the laboratory.
Parallel to the development of the SYNGEN program at the
computer, we have also a program in the laboratory for short syntheses
of various different natural products such as morphine, lysergic acid,
vitamin A, steroids, strychnine and other indole alkaloids. For all of
these we have created synthetic routes notably shorter and more
efficient that those which have already been done, following our aim in
showing the importance of an optimal synthesis plan.
Selected Publications
Hendrickson, J.B., DeVries J.G. 1982. A Convergent Total
Synthesis of the Coenzyme Methoxatin. J. Org. Chem 47: 1148.
Hendrickson, J.B. Hussoin, Md.S. 1987. Seeking the Ideal Dehydrating
Agent. J. Org. Chem. 52: 4137.
Hendrickson, J.B. 1990. Organic Synthesis in the Age of Computers.
Angew. Chem. Intl. Ed. 29: 1286.
Hendrickson, J.B. 1992. Descriptions of Reactions: their logic and
applications. Rec. Trav. Chim. Pays-Bas 111: 323.
Hendrickson, J.B., Sander, T. 1995. COGNOS: A Beilstein-type System for
Organizing Organic Reactions. Eur. J. Chem. 1: 449.
Hendrickson, J.B.,Shih, I-L. 1997. A New Approach to the Synthesis of
Cortical Steroids, J. Chinese Chem. Soc. 44: 133.
Hendrickson, J.B. 1997. Teaching Alternative Syntheses: The Syngen
Program," p. 214-231 in "Green Chemistry," ed. P. T. Anastas and T. C.
Williamson, ACS Symposium Series #626.
Hendrickson, J.B., Walker, M.A. 2000. A Two-Component Pericyclic
Reaction for Synthesis. Org. Letters 2: 2729-2731.
Computer Programs:
WebReactions.net Syngen2.chem.brandeis.edu