Abstract

Several classes of biologically active terpenes which contain a cyclooctane ring, typically within a bicyclo[6.3.0]undecane substructure, have been identified. These classes include antibiotics such as pleuromutilin and the ophiobolins, along with structurally simpler congeners such as dactyol. The synthesis of the central bicyclo[6.3.0]undecane carbocyclic skeleton via a novel, direct intramolecular[6Pi + 2Pi] photocycloaddition of 2-alkenyl tropones is described. A study of further transformations of these cycloadducts, including the total synthesis of dactylol, is proposed.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
5R01GM035727-02
Application #
3288856
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1986-07-01
Project End
1989-06-30
Budget Start
1987-07-01
Budget End
1988-06-30
Support Year
2
Fiscal Year
1987
Total Cost
Indirect Cost

  Institution

Name
Pennsylvania State University
Department
Type
Schools of Arts and Sciences
DUNS #
City
University Park
State
PA
Country
United States
Zip Code
16802

  Publications

Feldman, Ken S; Iyer, Malliga R (2005) Allenyl azide cycloaddition chemistry. synthesis of pyrrolidine-containing bicycles and tricycles via the possible intermediacy of azatrimethylenemethane species. J Am Chem Soc 127:4590-1
Feldman, Ken S; Vidulova, Daniela Boneva; Karatjas, Andrew G (2005) Extending Pummerer reaction chemistry. development of a strategy for the regio- and stereoselective oxidative cyclization of 3-(omega-nucleophile)-tethered indoles. J Org Chem 70:6429-40
Feldman, Ken S; Ngernmeesri, Paiboon (2005) Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment. Org Lett 7:5449-52
Feldman, Ken S (2005) Recent progress in ellagitannin chemistry. Phytochemistry 66:1984-2000
Feldman, Ken S; Karatjas, Andrew G (2004) Extending Pummerer reaction chemistry. Application to the oxidative cyclization of tryptophan derivatives. Org Lett 6:2849-52
Feldman, Ken S; Vidulova, Daniela Boneva (2004) Extending Pummerer reaction chemistry. Application to the oxidative cyclization of indole derivatives. Org Lett 6:1869-71
Feldman, Ken S; Iyer, Malliga R; Liu, Yanze (2003) Ellagitannin chemistry. Studies on the stability and reactivity of 2,4-HHDP-containing glucopyranose systems. J Org Chem 68:7433-8
Feldman, Ken S; Wilson, Sarah L; Lawlor, Michael D et al. (2002) In vitro and in vivo inhibition of LPS-induced tumor necrosis factor-alpha production by dimeric gallotannin analogues. Bioorg Med Chem 10:47-55
Feldman, Ken S; Eastman, Kyle J; Lessene, Guillaume (2002) Diazonamide synthesis studies: use of Negishi coupling to fashion diazonamide-related biaryls with defined axial chirality. Org Lett 4:3525-8
Feldman, K S; Sahasrabudhe, K; Lawlor, M D et al. (2001) In vitro and In vivo inhibition of LPS-stimulated tumor necrosis factor-alpha secretion by the gallotannin beta-D-pentagalloylglucose. Bioorg Med Chem Lett 11:1813-5

Showing the most recent 10 out of 13 publications