Diels-Alder Reactions of Silyloxyfurans: Scope and Limitations O O MeO
Scott Bur
O
Department of Chemistry Gustavus Adolphus College St. Peter, MN 56082
O
O O
OR
O
OMe
O O
O
OMe OMe
O
O OR
O
OR
R = TMS; TES; TBS; TIPS
O
or
OMe OMe
O OR
O
Rate: TMS > TES = TBS > TIPS
Understanding how factors that influence rates and diastereoselectivities of the intermolecular Diels-Alder reaction helps us design efficient intramolecular reactions.
N
OH O
O HO O
O OAc
Transition states for the favored diastereomers reveal a structural basis for diastereoselectivity
O
OH OH Fu-O
OH OH
OAc AcO
OAc
AcO
HO
O
n
R
R3SiO
n
R3SiO
O
R
R
R° H hypoglaunine B anti-HIV
We are developing an intramolecular approach to the core of biologically active natural products
