Towards the synthesis of hyacinthacines
Date
2012-02-10
Authors
Journal Title
Journal ISSN
Volume Title
Publisher
ORCID
Type
Degree Level
Masters
Abstract
The organocatalytic aldol reaction of tropinone with benzaldehyde using (S)-5-pyrrolidin-2-yl-1H-tetrazole as organocatalyst is described and it results in the formation of the dehydrated aldol adduct in moderate selectivity. The organocatalytic aldol reaction of CS and C2V-symmetrical dioxanones is also demonstrated and in most cases CS-symmetrical dioxanones offer a better stereoselectivity.
A new approach towards synthesis of hyacinthacine alkaloids: 2-epihyacinthacine A2, 3-epihyacinthacine A2 and their enantiomers is illustrated. The key step involves an organocatalytic aldol reaction of dioxanones where proline is used both as the catalyst and as the precursor for the aldehyde building block.
Description
Keywords
Organocatalytic aldol, tropinone, syn aldol, hyacinthacines
Citation
Degree
Master of Science (M.Sc.)
Department
Chemistry
Program
Chemistry