Abstract

This proposal outlines a strategy for the enantioselective synthesis of (-)- scarbronine A, a complex diterpenoid natural product. The scabronine compounds are potent stimulators of nerve growth factor-synthesis, making them potential therapeutic agents for a variety of nervous system disorders. The proposed strategy utilizes a novel coupling annulation to assemble the seven-membered ring.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of Neurological Disorders and Stroke (NINDS)
Type
Postdoctoral Individual National Research Service Award (F32)
Project #
5F32NS011150-02
Application #
6477292
Study Section
Medicinal Chemistry Study Section (MCHA)
Program Officer
Chiu, Arlene Y
Project Start
2000-12-01
Project End
2002-06-03
Budget Start
2001-12-01
Budget End
2002-06-03
Support Year
2
Fiscal Year
2002
Total Cost
$20,333
Indirect Cost

  Institution

Name
Sloan-Kettering Institute for Cancer Research
Department
Type
DUNS #
064931884
City
New York
State
NY
Country
United States
Zip Code
10065

  Publications

Mandal, Mihirbaran; Yun, Heedong; Dudley, Gregory B et al. (2005) Total synthesis of guanacastepene a: a route to enantiomeric control. J Org Chem 70:10619-37
Tan, Derek S; Dudley, Gregory B; Danishefsky, Samuel J (2002) Synthesis of the functionalized tricyclic skeleton of guanacastepene A: a tandem epoxide-opening beta-elimination/knoevenagel cyclization. Angew Chem Int Ed Engl 41:2185-8
Lin, Songnian; Dudley, Gregory B; Tan, Derek S et al. (2002) A stereoselective route to guanacastepene A through a surprising epoxidation. Angew Chem Int Ed Engl 41:2188-91
Dudley, G B; Danishefsky, S J (2001) A four-step synthesis of the hydroazulene core of guanacastepene. Org Lett 3:2399-402