Synthetic Strategies Toward Tetrahydrofurans Involving Double Diastereoselective Nucleophile-Promoted Aldol-Lactonizations and Subsequent Applications to Bioactive Natural Products
Abstract
Novel synthetic strategies towards the formation of tetrahydrofurans and their
subsequent application to bioactive natural products have been explored. More
specifically, a method for invoking double-diastereoselectivity in the formation of
tetrahydrofuran-fused β-lactones through nucleophile-catalyzed aldol-lactonization
(NCAL) has been developed. By employing a chiral catalyst, such as OTMS-quinidine
or OTMS-quinine, coupled with a chiral aldehyde acid substrate, we have been able to
successfully override the inherent substrate stereochemical bias to access either
diastereomeric product as the major adduct. This new methodology is being applied to
construction of the tetrahydrofuran fragment of the cytotoxic agent, haterumalide NA.
Subject
SynthesisDouble Diastereoselective
Tetrahydrofurans
Nucleophile Catalyzed Aldol Lactonization
Citation
Arendt, Kevin M. (2009). Synthetic Strategies Toward Tetrahydrofurans Involving Double Diastereoselective Nucleophile-Promoted Aldol-Lactonizations and Subsequent Applications to Bioactive Natural Products. Texas A&M University. Available electronically from https : / /hdl .handle .net /1969 .1 /ETD -TAMU -2009 -05 -806.