Chemical synthesis; synthesis-oriented organic chemistry; methods development; synthesis design; total synthesis of natural products.
Ph.D., organic chemistry, The Scripps Research Institute
A.B., chemistry, Harvard University
postdoc, chemical synthesis, Princeton University
Awards and Academic Honors
NIH NRSA (F32) post-doctoral fellowship
NIH NRSA (F31) pre-doctoral fellowship
The challenges confronting synthetic organic chemists are two-fold: 1) they must refine their craft to improve the overall efficiency of synthetic sequences and endeavors and 2) they must discover or devise state-of-the-science chemical technology in order to address the assembly of novel molecular architectures. In particular, the goals of academic chemical synthesis are to address stereochemical complexity, unusual connectivity/topology, and unknown reactivity. Natural product synthesis has traditionally served as a measure of achievement with such concerns in mind. However, to stave off stagnation in this vibrant research area, chemists must address the synthesis of challenging natural products in new ways. Specifically, the total synthesis of natural products using only clever synthetic design - manifested by artistic orchestration of pre-existing methodologies - is a necessary but insufficient condition for advancing the field; new chemical methods of broad generality must be fashioned and their worth demonstrated in the most demanding of contexts. We expect that our laboratory will offer solutions to longstanding problems in chemical synthesis that blend judicious synthesis planning with new and innovative bond constructions. Our research will expand the scope of known reactivity and possibly enable studies of biological phenomena.
Primary Research Area
- Baran, P. S.; Guerrero, C. A.; Ambhaikar, N. B.; Hafensteiner, B. D. "Short, Enantioselective Total Synthesis of Stephacidin A." Angew. Chem. Int. Ed. 2005, vol. 44, 606-609.
- Baran, P. S.; Guerrero, C. A.; Corey, E. J. "Short, Enantioselective Total Synthesis of Okaramine N." J. Am. Chem. Soc. 2003, vol. 125, 5628-5629.
- Baran, P. S.; Guerrero, C. A.; Corey, E. J. "The First Method for Protection-Deprotection of the Indole 2,3-(pi) Bond." Org. Lett. 2003, vol. 5, 1999-2001.
- Baran, P. S.; Guerrero, C. A.; Hafensteiner, B. D.; Ambhaikar, N. B. "Total Synthesis of Avrainvillamide (CJ-17,665) and Stephacidin B." Angew. Chem. Int. Ed. 2005, vol. 44, 3892-3895.
- Baran, P. S.; Hafensteiner, B. D.; Ambhaikar, N. B.; Guerrero, C. A.; Gallagher, J. D. "Enantioselective Total Synthesis of Avrainvillamide and the Stephacidins." J. Am. Chem. Soc. 2006, vol. 128, 8678-8693.
- Guerrero, C. A.; Sorensen, E. J. "Concise, Stereocontrolled Synthesis of the Citrinadin B Core Architecture." Org. Lett. 2011, vol. 13, 5164-5167.
- Shenvi, R. A.; Guerrero, C. A.; Shi, J.; Li, C.-C.; Baran, P. S. "Synthesis of (+)-Cortistatin A." J. Am. Chem. Soc. 2008, vol. 130, 7241-7243.
- Shi, J.; Manolikakes, G.; Yeh, C.-H.; Guerrero, C. A.; Shenvi, R. A.; Shigehisa, H.; Baran, P. S. "Scalable Synthesis of Cortistatin A and Related Structures." J. Am. Chem. Soc. 2011, vol. 133, 8014-8027.
- Shi, J.; Shigehisa, H.; Guerrero, C. A.; Shenvi, R. A.; Li, C.-C.; Baran, P. S. "Stereodivergent Synthesis of 17-(alpha)- and 17-(beta)-Aryl Steroids: Application and Biological Evaluation of D-Ring Cortistatin Analogues." Angew. Chem. Int. Ed. 2009, vol. 48, 4328-4331.