Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
229764 | Journal of Saudi Chemical Society | 2013 | 14 Pages |
Abstract
Setting up the correct functionality with the correct stereochemistry in the ring-A of anthracycline precursors represents a synthetic challenge. The use of d-glucose as a chiral auxiliary either on the silyloxy diene or naphthoquinone-based dienophile to form the ring-A using asymmetric Diels–Alder reactions as developed by the Stoodley group and is the focus of this review. The endo-transition state is described based on a frontier orbital approach and the HOMO–LUMO energy gaps were estimated using semi-empirical (MNDO) calculations with SPARTAN’08. As anthracyclines are used in chemotherapy, some of their associated biochemistry and clinical effectiveness are also briefly introduced.
Related Topics
Physical Sciences and Engineering
Chemical Engineering
Chemical Engineering (General)
Authors
Jonathan P. Miller, Richard J. Stoodley,