The goal of this program is to define new strategies and methods for the synthesis of bioactive molecules in the diterpenoid alkaloid family. The complex molecules that we construct can provide tools to study ion channels and may ultimately be used to develop new therapeutics. Our synthetic studies should also lead to a better understanding of organic functional group reactivity since our targets possess a multitude of functional groups in a congested setting. Specifically, we intend to develop strategies to synthesize different structural classes of diterpenoid alkaloids including coryphine, kobusine and cossonidine. We expect our unique strategies and methods for synthesis to streamline access to unique ion channel potentiators.

Public Health Relevance

Finding new and more efficient ways to construct complex small molecules derived from natural products is an important pursuit that may lead to improvements in human health. Our goals are to develop new strategies and methods that efficiently build complex natural products in the diterpenoid alkaloid family and their associated derivatives of pharmaceutical relevance that would positively address neurodegenerative diseases.

National Institute of Health (NIH)
National Institute of General Medical Sciences (NIGMS)
Research Project (R01)
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Special Emphasis Panel (ZRG1-BCMB-R (02))
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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