The [4+4] photodimerization of 2-pyridones is as efficient method for preparing cyclooctadienes strategically functionalized for synthetic challenges such as taxol and the fusicoccanes. This single-step method for preparing complex structure from simple aromatic precursors proceeds with high region- and stereochemical control, but has not been exploited synthetically. Our studies of a previously untested intramolecular version of this reaction has laid the groundwork for applications to total synthesis. Two intramolecular approaches to taxol, and a synthesis of the complex fusicoccane are proposed. A preliminary study has demonstrated a selective intermolecular reaction of 4-alkoxy-2-pyridone with 2-pyridone, predicated on the inability to undergo [4+4] photodimerization. This new approach to control of the [4+4] reaction, in the absence of a tether, allows for other important targets to be addressed. Synthesis of the antibiotic pentalenolactone and an approach to taxol are proposed.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
2R01GM045214-04A1
Application #
2183005
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1991-01-01
Project End
1998-06-30
Budget Start
1994-07-01
Budget End
1995-06-30
Support Year
4
Fiscal Year
1994
Total Cost
Indirect Cost
Name
State University New York Stony Brook
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
804878247
City
Stony Brook
State
NY
Country
United States
Zip Code
11794