Abstract

Both the recent resurgence of infectious disease and the abiding interest in new tools for neuropharmacology have driven the continuing effort to isolate and establish the structures of new active agents from natural sources. While some of these might well be useful leads for pharmaceutical development, often the structurally more complex agents will not be pursued, because of perceived difficulties with their synthesis. An investigation of a new method for the construction of carbocyclic rings, intramolecular alkylidene C-H insertion, is proposed. This already shows the promise of becoming a powerful tool for target-directed synthesis. Specific targets include the cognition-enhancing alkaloid huperzine A, morphine, the parent compound of the morphine alkaloids, and N-deacetyllappaconitine, representative of the Delphinium diterpenoid alkaloids.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM060287-03
Application #
6520121
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Schwab, John M
Project Start
2000-04-01
Project End
2004-03-31
Budget Start
2002-04-01
Budget End
2003-03-31
Support Year
3
Fiscal Year
2002
Total Cost
$205,406
Indirect Cost

  Institution

Name
University of Delaware
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
059007500
City
Newark
State
DE
Country
United States
Zip Code
19716

  Publications

Taber, Douglass F; Berry, James F (2013) Construction of the tricyclic A-B-C core of the Veratrum alkaloids. J Org Chem 78:8437-41
Taber, Douglass F; DeMatteo, Peter W (2012) A piperidine chiron for the Veratrum alkaloids. J Org Chem 77:4235-41
Taber, Douglass F; Gerstenhaber, David A; Berry, James F (2012) Correction to enantioselective conjugate allylation of cyclic enones. J Org Chem 77:1215
Taber, Douglass F; Raciti, David M (2011) Synthesis of (-)-Astrogorgiadiol. Tetrahedron 67:10229-10233
Taber, Douglass F; Tirunahari, Pavan K (2011) Indole synthesis: a review and proposed classification. Tetrahedron 67:7195-7210
Taber, Douglass F; Bai, Sha; Tian, Weiwei (2011) Synthesis of the reported structure of trans-africanan-1?-ol. J Org Chem 76:9733-7
Taber, Douglass F; Nelson, Christopher G (2011) Aliphatic C-H to C-C conversion: synthesis of (-)-cameroonan-7?-ol. J Org Chem 76:1874-82
Taber, Douglass F; Guo, Pengfei; Pirnot, Michael T (2010) Conjugate addition of lithiated methyl pyridines to enones. J Org Chem 75:5737-9
Taber, Douglass F; Paquette, Craig M; Reddy, P Ganapati (2009) One Carbon Homologation of Halides to Benzyl Ethers. Tetrahedron Lett 50:2462-2463
Taber, Douglass F; Sheth, Ritesh B; Tian, Weiwei (2009) Synthesis of (+)-coronafacic acid. J Org Chem 74:2433-7

Showing the most recent 10 out of 39 publications