The goal of this program is to define new strategies and methods for the synthesis of bioactive molecules. The small molecules that we construct can provide tools to study biological processes and may ultimately be used to develop new therapeutics. These studies will also lead to a better understanding of organic functional group reactivity. Specifically, we intend to develop a general strategy for the synthesis of the sesterterpene compounds neomangicol C and mangicol A. These compounds possess antitumor, antibacterial and anti-inflammatory properties. We also present a novel iodine-mediated pentannulation reaction that will be applied to the synthesis of a series of resveratrol-derived natural products. It is our anticipation that these new methodological developments for pentannulation will streamline the synthesis of complex molecules. The total synthesis of the natural products drives the development of new methods and strategies. In turn, these new developments will be applied to the synthesis of other molecules of biological and structural interest. These contributions will aid advances in human medicine and chemical biology by providing a synthesis foundation.

Public Health Relevance

Finding new and more efficient ways to construct small molecules is an important pursuit that will provide new tools for chemical biology and medicine and lead to improvements in human health. Our goals are to develop new strategies and methods that efficiently build small molecules that are of pharmaceutical importance and natural products. In this regard, we are especially interested in new five-membered ring forming reactions using transition metals.

National Institute of Health (NIH)
National Institute of General Medical Sciences (NIGMS)
Research Project (R01)
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Synthetic and Biological Chemistry B Study Section (SBCB)
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Lees, Robert G
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University of California Berkeley
Schools of Arts and Sciences
United States
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Schultz, Erica E; Lindsay, Vincent N G; Sarpong, Richmond (2014) Expedient synthesis of fused azepine derivatives using a sequential rhodium(II)-catalyzed cyclopropanation/1-aza-Cope rearrangement of dienyltriazoles. Angew Chem Int Ed Engl 53:9904-8
Heller, Stephen T; Kiho, Toshihiro; Narayan, Alison R H et al. (2013) Protic-solvent-mediated cycloisomerization of quinoline and isoquinoline propargylic alcohols: syntheses of (ýý)-3-demethoxyerythratidinone and (ýý)-cocculidine. Angew Chem Int Ed Engl 52:11129-33
Lebold, Terry P; Wood, Jessica L; Deitch, Josh et al. (2013) A divergent approach to the synthesis of the yohimbinoid alkaloids venenatine and alstovenine. Nat Chem 5:126-31
Hardin Narayan, Alison R; Sarpong, Richmond (2012) Indolizinones as synthetic scaffolds: fundamental reactivity and the relay of stereochemical information. Org Biomol Chem 10:70-8
Lian, Yajing; Miller, Laura C; Born, Stephen et al. (2010) Catalyst-controlled formal [4 + 3] cycloaddition applied to the total synthesis of (+)-barekoxide and (-)-barekol. J Am Chem Soc 132:12422-5
Simmons, Eric M; Hardin-Narayan, Alison R; Guo, Xuelei et al. (2010) Formal total synthesis of (+/-)-cortistatin A. Tetrahedron 66:4696-4700
Jeffrey, Jenna L; Sarpong, Richmond (2009) An approach to the synthesis of dimeric resveratrol natural products via a palladium-catalyzed domino reaction. Tetrahedron Lett 50:1969-1972
Larson, Kimberly K; Sarpong, Richmond (2009) Total synthesis of alkaloid (+/-)-G. B. 13 using a Rh(I)-catalyzed ketone hydroarylation and late-stage pyridine reduction. J Am Chem Soc 131:13244-5
Jeffrey, Jenna L; Sarpong, Richmond (2009) Concise synthesis of pauciflorol F using a Larock annulation. Org Lett 11:5450-3
Wood, Jessica L; Pujanauski, Brian G; Sarpong, Richmond (2009) Synthesis of the tetracyclic core of the neomangicols using a late-stage indene alkylation. Org Lett 11:3128-31