Jon D. Rainier
Associate Professor of Chemistry
B.S. University of California, Irvine
Ph.D. University of California, Riverside
Research
Our
primary interests lie in the field of chemical synthesis. Within
this discipline, we are particularly fascinated by the interplay
between structure (biological activity), total synthesis, and the
development of new chemical reactions.
Total Synthesis and Structure
Biologically active targets that are currently receiving attention
in our laboratory include: (a) fused polycyclic ether natural products
(e.g. the neurotoxic marine natural product gambierol and the potent
anticancer agent halichondrin B); (b) indoline and oxindole natural
products (e.g. ditryptophenaline, cytochalasin); (c) oxygenated
cembranoids (e.g. the anticancer agent eleutherobin); (d) Diazofluorenone
containing natural products (e.g. the anticancer agent lomaiviticin).
Reaction
Development
We are also involved in the development of new reactions with a
particular emphasis on the use of new and/or improved methods to
the synthesis of the targets mentioned above. Among the reactions
currently being examined in our laboratory are: (a) new methods
to synthesize carbon-glycosides; (b) ring-closing and ring opening
metathesis reactions; (c) the use of rhodium carbenoids to generate
highly substituted indolines; (d) ring expansion reactions of bicyclic
ring systems; (e) metal induced [2+2+1] cycloaddition reactions.
References
1. Novikov AN, Kennedy AR, Rainier JD (2003) Sulfur Ylide Initiated
Thioclaisen Rearrangements. The Synthesis of Highly Substituted
Indolines. J. Org. Chem. 68:993
2. Majumder U, Cox JM, Rainier JD (2003) Synthesis of an F-H Gambierol
Subunit Using a C-Glycoside Centered Strategy. Org. Lett. 4:913
3. Weerasakere M, Xu Q, Rainier JD (2002) An Anionic Condensation
and Fragmenta-tion Approach to 3-Pyrrolines. Tetrahedron Lett. 43:8913
4. Allwein SP, Cox JM, Howard BE, Johnson H, WB, Rainier JD (2002)
C-Glycosides to Fused Polycyclic Ethers. Tetrahedron 58:1997
5. Imbriglio JE, Rainier JD (2001) [2+2+1] Cycloadditions of Ynol
Ethers. The Synthesis of Iron Complexes of 3-Alkoxycyclopentadie-nones.
Tetrahedron Lett. 42:6987
6.
Cox JM, Rainier JD (2001) C-Glycosides to Fused Polycyclic Ethers.
An Efficient Entry into the A-D Ring System of Gambierol. Org. Lett
3:2919
7. Xu Q, Weeresakare M, Rainier JD (2001) Anionic Ring Expansion
Reactions of Oxabicyclo[4.2.1]heptenones. An Efficient Entry into
the Carbon Framework of Oxygenated Cembranoids. Tetrahedron 57:8029
8. Rainier JD, Cox JM, Allwein SP (2001) Enol Ether-Olefin Ring
Closing Metathesis Using the Grubbs Ruthenium Imidazole Catalyst.
Tetrahedron Lett. 42:179
9. Rainier JD, Allwein SP, Cox JM (2001) C-Glycosides to Fused Polyethers.
A Formal Synthesis of (±)-Hemibrevetoxin B. J. Org. Chem.
66:1380
